“Lord, give me chastity and self-control — but not yet.”

— Prayer of the young Saint Augustine, c.380 A.D.

The scandals may be coming thick and strong from the Vatican at the moment, but the Church has always waged a losing battle with its own vice-ridden staff. The problem was that transgressions from official policy often began at the top. Fellow priests put one of the first popes, Sixtus III (432-40), on trial for seducing a nun. He was acquitted after quoting from Christ in his defense: “Let you who are without sin cast the first stone.” In the centuries to follow, political skullduggery and a corrupt election process thrust one improbable candidate after another into the position as god-fearing believers looked on in impotent horror. In fact, so many Vicars of Christ have been denounced as the “Worst Pope Ever” that we have to settle for a Top Ten list.

1. Sergius III (904-11), known by his cardinals as “the slave of every vice,” came to power after murdering his predecessor. He had a son with his teenage mistress — the prostitute Marozia, 30 years his junior — and their illegitimate son grew up to become the next pope. With top Vatican jobs auctioned off like baubles, the papacy entered its “dark century.”

2. The 16-year-old John XII (955-64) was accused of sleeping with his two sisters and inventing a catalog of disgusting new sins. Described by a church historian as “the very dregs,” he was killed at age 27 when the husband of one of his mistresses burst into his bedroom, discovered him in flagrante, and battered his skull in with a hammer.

3. Benedict IX, (1032-48) continually shocked even his most hardened cardinals by debauching young boys in the Lateran Palace. Repenting of his sins, he actually abdicated to a monastery, only to change his mind and seize office again. He was “a wretch who feasted on immorality,” wrote Saint Peter Damian, “a demon from hell in the disguise of a priest.”

Boniface VIII



4. After massacring the entire population in the Italian town of Palestrina, Boniface VIII (1294-1303) indulged in ménages with a married woman and her daughter and became renowned through Rome as a shameless pedophile. He famously declared that having sex with young boys was no more a sin than rubbing one hand against the other — which should make him the patron saint of Boston priests today. The poet Dante reserved a place for him in the eighth circle of Hell.

5. All pretense at decorum was abandoned when the papacy moved to Avignon in southern France for 75 years. Bon vivant Clement VI (1342-52) was called “an ecclesiastical Dionysus” by the poet Petrarch for the number of mistresses and the severity of his gonorrhea. Upon his death, 50 priests offered Mass for the repose of his soul for nine consecutive days, but French wits agreed that this was nowhere near enough.

Sixtus IV



6. Decamping back to Rome, the papacy hit its true low point in the Renaissance. (Church historian Eamon Duffy compares Rome to Nixon’s Washington, “a city of expense-account whores and political graft.”) Sixtus IV (1471-84), who funded the Sistine Chapel, had six illegitimate sons — one with his sister. He collected a Church tax on prostitutes and charged priests for keeping mistresses, but critics argued that this merely increased the prevalence of clerical homosexuality.

Innocent VIII



7. The rule of Innocent VIII (1484-92) is remembered as the Golden Age of Bastards: He acknowledged eight illegitimate sons and was known to have many more, although he found time between love affairs to start up the Inquisition. On his death bed, he ordered a comely wet nurse to supply him with milk fresh from the breast.

Alexander VI



8. The vicious Rodrigo Borgia, who took the name Alexander VI (1492-1503), presided over more orgies than masses, wrote Edward Gibbon. A career highlight was the 1501 “Joust of the Whores,” when 50 dancers were invited to slowly strip around the pope’s table. Alexander and his family gleefully threw chestnuts on the floor, forcing the women to grovel around their feet like swine; they then offered prizes of fine clothes and jewelry for the man who could fornicate with the most women. Alexander’s other hobbies included watching horses copulate, which would make him “laugh fit to bust.” After his death — quite possibly poisoned by his pathological son, Cesar Borgia — this pope’s body was expelled from the basilica of Saint Peter as too evil to be buried in sacred soil.

Julius II



9. Julius II (1503-13) is remembered for commissioning Michelangelo to paint the Sistene Chapel’s ceiling. He was also the first pope to contract “the French disease,” syphilis, from Rome’s male prostitutes. On Good Friday of 1508, he was unable to allow his foot to be kissed by the faithful as it was completely covered with syphilitic sores.

10. Incurable romantic Julius III (1550-55) fell in love with a handsome young beggar boy he spotted brawling with a vendor’s monkey in the streets. The pope went on to appoint this illiterate 17-year-old urchin a cardinal, inspiring an epic poem, “In Praise of Sodomy,” probably written by a disgruntled archbishop in his honor. • 11 May 2010