Random Popes Who Didn't Take Celibacy Very Seriously (10 items)

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  (#2) Paul II Allegedly Passed While Sexually Engaged With A Male Page

  Paul II was a 15th-century pope who was engaged in minor conflicts for his seven-year tenure. Celibacy may have been an issue, as the manner and circumstances of his passing are disputed. Official accounts have him succumbing to heart failure after eating an excessive amount of melon.

  Other accounts, possibly originating with papal enemies, assert that Paul II passed during the intimate act of a young male page entering him from the rear. That he thoroughly enjoyed dressing up in elaborate vestments also contributed to rumors of "effeminacy" and homosexuality.    
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  (#1) Pope Alexander VI Fathered Nine Children

  Rodrigo de Borja, AKA Pope Alexander VI, brought misconduct within the Catholic Church to unprecedented levels. Connected to the Spanish branch of the powerful Borgia ecclesiastical dynasty, he was appointed a cardinal by his uncle and eventually became the vice-chancellor of the Catholic Church, acquiring tremendous wealth by selling offices and indulgences to the wealthy.

  He didn't even maintain the pretense of celibacy, ultimately acknowledging four children with his upper-class Roman mistress Vannozza Catanei. He had five other children from various other mistresses, children he claimed as nieces or nephews.

  His son Cesare (the model for Machiavelli's The Prince) would resign his cardinalate and marry a French noblewoman. Alexander's daughter Lucrezia would engage in various notorious affairs and three marriages; historical speculation has abounded about her also engaging in intrafamilial relations.
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  (#6) Pope Benedict IX Was 'A Demon From Hell In The Disguise Of A Priest'

  By all accounts, Benedict IX was not only a really bad pope - he was a really bad person. A contemporary called him a "demon from hell in the disguise of a priest." Even the Catholic Encyclopedia, which is frequently accused of sanitizing papal history, refers to him as a "disgrace to the chair of St. Peter." One of the youngest popes ever elected, in 1032 he immediately began spending the papal treasury in bordellos and on debauchery, hosting group sexual engagements that included men and animals. 

  His behavior was shocking even by Roman standards: his first papacy ended when angry Romans rebelled and expelled him briefly in 1036. He would exploit politics and be re-installed, only to be removed again in 1044. Benedict assembled an army and retook the papacy a third time in 1047. Wisely, considering his unpopularity, he decided to sell the papacy and get married. Typically, he soon changed his mind, throwing the political situation into chaos.

  He would eventually be forcibly expelled and excommunicated, after which he renounced his ways and later passed in a monastery in 1056. He is the only pope with three separate terms in the office and the only pope to openly auction off the position.
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  (#8) Leo X, The First Medici Pope, Was Also Actively Gay

  Julius II's successor was Leo X, the first Medici pope, the son of Lorenzo Medici, called "Il Magnifico." His father cautioned him against the licentious atmosphere in Rome: 

  You ought to be grateful to God, and continually to recollect that it is not through your merits, your prudence, or your solicitude, that this event has taken place, but through his favor, which you can only repay by a pious, chaste and exemplary life.

  Maintaining such a virtuous lifestyle would, though, be difficult in Rome, "that sink of all iniquity." Giovanni would "probably meet with those who will particularly endeavor to corrupt and incite you to vice." Unfortunately, Leo X continued the money-raising practice of selling both indulgences and offices.  He is also mentioned in two contemporary histories as having had routine involvement with male lovers, and he is listed as such in a modern who's who of gay history. 
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  (#10) Pope Leo XII Slept With The Wife Of A Swiss Guard And Fathered At Least Three Children

  Born Annibale della Genga, Leo XII was one of the most conservative and unpopular popes of the 19th century. In his six-year reign starting in 1823, he instituted many laws and ordinances including prohibiting Jews from owning personal property, banning alcohol in Rome, and reintroducing regulations not seen since the Middle Ages. He was elected pope despite his ill health; in fact, he was a compromise candidate who most believed would not survive for any length of time. 

  Assigned by Pius VI in 1794 as papal nuncio to France, Austria, and several German states, he is believed to have conceived three illegitimate children in a dalliance with the wife of a Swiss Guard. Believing that this would be his final appointment in the church seems to have given him a fatalistic attitude towards his holy obligations. He would live in poor health for another three decades, finally succumbing in 1829. 
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  (#9) Pope Paul III Openly Flouted Celibacy While A Young Man

  Alessandro Farnese (Pope Paul III) was a member of the wealthy and powerful house of Farnese, an influential Italian family during the Renaissance. His sister Giulia was reportedly the mistress of Pope Alexander VI. Farnese's youthful appointment as a cardinal was the result of this relationship.

  In his youth, Alessandro paid no attention to vows of celibacy, openly having five children with a mistress named Silvia Ruffini. All of these children would be recognized as his offspring and would achieve high positions of nobility in Italian society, most notably his son Pier Luigi Farnese, the first Duke of Parma.

  Although his children would be officially acknowledged in 1513, Farnese broke off his relationship with his mistress when he ascended to the papacy in 1534. As pope, he is most famous for excommunicating Henry VIII and commissioning numerous projects of Michelangelo.

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