Benedict IX
Benedict IX is the only pope to serve three times (October 1032-September 1044, then April 1045-May 1045 and finally November 1047-July 1048). A member of a powerful family, his father bribed, manipulated and threatened the Roman clergy to have his 17-year-old son elected pope although the boy had no priestly experience or training. In the Liber Gomorrhianus, St. Peter Damian describes him as “feasting on immorality” and “a demon from hell in the disguise of a priest” guilty of bribery, orgies and open sexual perversion, including bestiality. Most historians cite Benedict IX as the worst in the history of the papacy. After leaving office three times amid various scandalous intrigues, he was forced to flee to the Abbey of Grottaferrata, where he repented of his sins and spent the rest of his life doing penance. The next popes introduced many reforms, such as making the cardinals the papal electors. Benedict IX is definitely a pope that the church would prefer to forget.