#6 Boniface VIII
Pope Boniface VIII (1294-1303) didn’t want to save your soul; he wanted to rule your life. Boniface VIII was one of the most ardent supporters of papal authority. What started as a minor squabble with King Philip IV of France over a government’s ability to tax clergy members escalated until Boniface VIII excommunicated the king and released a decree stating that “every human creature [was] subject to the Roman pontiff.” Boniface VIII sent mercenaries to destroy other people’s castles, declared all the prominent Italian Colonna family’s property forfeited and proceeded to parcel their land out among his family members. In September 1303, an army led by the Colonna family kidnapped the Pope and demanded that he abdicate. Held in captivity for multiple days, the Pope refused. He survived the attack and returned to Rome only to die a month later.
Although Boniface VIII was still alive when Dante — who had been personally exiled by the Pope for supporting papal limitations — wrote his famous Divine Comedy, the Italian writer placed him in his version of Hell anyway.
#5 Benedict IX
Pope Benedict IX was not exactly beloved. St. Peter Damian, for one, called him a “demon from hell in the disguise of a priest.” In his third book of Dialogues, Pope Victor III wrote of Benedict IX as having a “life as a pope so vile, so foul, so execrable, that I shudder to think of it.” No wonder Benedict IX decided to stick it to all of them, resigning in 1045 — and becoming the first man in history to sell the papacy. The buyer: the priest John Gratian (Pope Gregory VI). Benedict IX later refused to face charges of simony and was excommunicated.