Some were controversial because of the reforms they brought in (or tried to bring in) - like Gregory I or Gregory VII. But even these were probably not as controversial as the following.
Note that most of them fall during the period of the papal states (754–1870) when popes were often more like kings than bishops - and it showed.
In chronological order:
Pope Liberius (352–66). About the only pope in the first five hundred years of the papacy not considered a saint, for supposedly falling into Arian heresy after being exiled from Rome by secular powers.
Formosus (891–96) - for breaking ancient canon law and abandoning his previous church as bishop, to come to Rome. As if it were a promotion or something!
Stephen VI (896–97) - for digging up Formosus months after his death and putting him on trial. In full pontifical regalia. Then chopping off his fingers and throwing his body into the Tiber.
Pretty much every pope from Sergius III (904–11), who fathered a child on a teenage prostitute (who later became pope, himself) to John XII (955-64) who was murdered when caught in bed with another man’s wife. They call this the Dark Age (saeculum obscurum) of the papacy.
Benedict IX (1032–44; 1045; 1047–48) served three terms, starting at the age of about 20, and was guilty of bribery, simony, adultery and was accused of murder, rape, and pedophilia. He was expelled from Rome in 1044, sold the papacy in 1045, and deposed by a Council in 1048.
Boniface VIII (1294–1303) was famously placed in the eighth circle of hell by Dante. He was posthumously tried for heresy, and accused of all manner of sins, including mass murder (he ordered the razing of Palestrina, home to some 6000 souls - how many were massacred vs how many escaped is unclear).
Pretty much all the popes of the so-called Avignon Papacy (1309–1376) - the very idea of the bishop of Rome living out of Rome is bad enough, but the kind of lifestyle lived there had little to do with Christianity. Indulgence, materialism, mistresses…
Sixtus IV (1471–84) - of Sistine Chapel fame and involvement in the Pazzi conspiracy- had several illegitimate children, nepotism,
Alexander VI Borgia (1492–1503) is famously not included among the popes buried in St. Peters - even some of those above are - as he was considered so manifestly not Christian as to not be buried in holy ground. They have made an HBO series about his decadence.
Julius II (1503–13) though beloved by art historians for his patronage of Michelangelo was a warrior pope and nicknamed “the terrible”…. though, even he felt that the Borgia popes had been so evil that he sealed their apartments, and ordered the name of the Borgias to be stricken from records and arts, on pain of excommunication.
Leo X (1513–1521) was the last “lay” cardinal to be elected pope. Most well known for approving the idea that indulgences could be sold as a capital campaign for the new St. Peter’s basilica, excommunicating Martin Luther while on a hunting trip, and declaring that his predecessors did not know how to properly enjoy the papacy - which he did so well that he bankrupted the papal treasury. One of his modern successors (Benedict XVI) all but declared him a failure as pope at a crucial moment of Church history.
Pius IX (1846–1878) though personally holier by far than most of the rest of this list, resented Italian nationalism, ordered a young Jewish child kidnapped from his family because he had been secretly baptized by the nanny, and bullied the world’s bishops into a Council declaring himself infallible, so that his favorite doctrine of Mary (Immaculate Conception) could be declared as such ex post facto. He issued the famous syllabus of errors. When the Italians took over Rome, he spent the rest of his papacy pouting in self-imposed house arrest. He was so unpopular by the time he died that there were riots in the streets and, despite a secret nighttime funeral procession, Romans attempted to throw his remains into the Tiber.
Finally, Pope Francis (2013-ad multos annos!) for saying that killing is against the gospel, that bishops should exercise their ministry as governors of the Church, that sacramental discipline can actually change, and that love and mercy is the key to understanding God. Oh, and for eschewing the materialistic trappings of power and privilege that have accrued to the papacy by some of the folks mentioned above.
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