17 Popes Who Didn’t Practice What They Preached

16. The Church Put Pope Sixtus III on Trial for Seducing a Nun

The Catholic Church has tossed around the idea of celibacy since the fourth century, but it didn’t quite catch on for many centuries. However, there were certain things that popes shouldn’t do. In an otherwise blemish-free pontificate from 432-440, Pope Sixtus III stood trial on the charge of seducing a nun. Surprising the church court, the pope used the words of Christ as inspiration for his defense. In John 8:7, when the Pharisees condemned an adulterous woman in from of him, Jesus declared to the people, “He that is without sin among you, let him cast the first stone at her.”

During his trial, Pope Sixtus III stood up and promptly declared the same: “Let you who are without sin cast the first stone.” Whether or not the pope’s defense was his confession is unclear. Chances are he didn’t take the trial seriously, for the judges probably committed the same crime. Although the fifth-century sources are lean, the court could not find any proof that Sixtus had seduced the nun. Without evidence, the trial ended. Keeping a clean reputation after the trial, Sixtus III wrote an essay on the virtues of chastity before his death in 440. Whether or not he was guilty is anyone’s guess.

15. Cardinal Alessandro Farnese Openly Acknowledged His Mistress and Children Long Before His Election as Pope Paul III

During his affair with Giulia Farnese, Pope Alexander VI elected her brother, Alessandro, to the College of Cardinals. Known as the “Petticoat Cardinal,” Alessandro and his mistress, Silvia Ruffini, had five children together. Incredibly proud of his family, he never hid his children or his relationship. Alessandro publicly acknowledged his offspring in 1513, over twenty years before his election to the papacy. Pope Paul III set aside his mistress, but he remained devoted to his children and his grandchildren during his pontificate.

The pope with a large extended family still considered himself a moral reformer. Paul established a special council to privately investigate the corruption within the Catholic Church in March 1537. Someone leaked the report to the leaders of the Protestant Reformation, who used the details in their movement. The pope also excommunicated King Henry VIII of England over his “Great Matter” – divorcing his wife of over two decades, Catherine of Aragon, to marry his mistress, Anne Boleyn.

Using the nepotism of most Renaissance popes, Paul appointed his son Pierluigi as the governor of Piacenza, and he elected two of his grandsons to the College of Cardinals. After the disgruntled population assassinated Pierluigi during an uprising, Paul wanted to place the city under papal jurisdiction. His grandson, Ottavio, claimed the governorship as his inheritance, refusing to give control of Piacenza to the pope. The extremely offended Paul summoned Ottavio to his presence in Rome. When he arrived, the heated confrontation between grandfather and grandson was too much for the eighty-two-year-old Paul; he died hours later.

14. Through His Affair with a Black Maid, Clement VII Became the Ancestor of the Modern Elite

One of the unluckiest popes in history, Giulio de Medici – the cousin of Leo X – was elected Pope Clement VII during a time of political turmoil in Europe. In 1523, the Protestant Reformation was well under way, gaining popularity throughout Europe. Although he tried to play the political role of his predecessors, Clement did not understand how to navigate the new world of religious change. At the center of a power struggle between Protestant and Catholic kings, Clement’s reign as pope was somewhat disappointing. However, through an affair with a family servant, he left a permanent legacy: his descendants appear in the present-day modern European elite.

Pope Clement’s colleagues regarded him as a morally upright, devout representative of the Church throughout his pontificate. However, before taking holy orders, he had an affair with the family maid, Simonetta da Collevecchio, resulting in the birth of his son Alessandro de Medici. Clement’s nephew, Lorenzo II de Medici, assumed paternity of the child; although his contemporaries acknowledged Alessandro as Lorenzo’s son, later historians claim that it is far more likely that Clement was Alessandro’s father. The mixed-race Alessandro inherited the nickname “the Moor” because of his darker skin tone.

Through the patronage of his father, Clement VII, Alessandro would ascend to great power, becoming the first black head of state of the modern Western world. Installing his son as the Duke of Florence, Clement assured that the city-state remained in the family’s hands. Alessandro married the illegitimate daughter of the Holy Roman Emperor Charles V, but their short union was childless. He had one mistress, Taddea Malaspina, with whom he fathered two children: Giulio de Medici and Giulia de Medici. Through Alessandro’s descendants, several members of the European nobility can trace their ancestry back to a pope.

13. Innocent VIII Was the First Pope to Acknowledge His Illegitimate Children Openly

Cardinal Giovanni Cibo lived a worldly life before the curia elected him Innocent VIII in 1484. In a fairly unimpressive papacy, the elderly pope became the first pontiff to publicly announce that he fathered illegitimate children. Using his influence to provide for his offspring, Innocent set a precedent for his successors. The pope was extremely lazy, only working when he had to do so. Securing wealth, land, and advantageous marriages for his children seemed to be the only work he had any energy to accomplish. Granting his problematic son Franceschetto some decent titles, such as the governor of Rome, Innocent arranged a strategic marriage for his son into the prominent Medici family.

Franceschetto had expensive tastes, and his father funded his lifestyle with papal money. Innocent also married his daughter, Teodorina Cibo, to an Italian nobleman. Although there is little evidence that he continued his affairs into his pontificate, Innocent never lost his love for women. Before his death, his love for excess, especially food, made him grossly overweight. In the days before he died, Innocent could only drink a few drops of milk for sustenance. Rumor has it that he ordered a beautiful wet nurse to stand at his bedside so that he could enjoy her milk from the source.

12. Julius III Fell in Love with a Street Urchin and Made Him a Cardinal

In 1548, Giovanni Ciocchi Del Monte, the future Julius III, fell in love with a homeless boy on the streets of Parma. Innocenzo was fifteen years old when Giovanni took him off the streets, forcing his brother to adopt him and bring him into his household. The cardinal carried on a relationship with Innocenzo for two years, until he was elected pope in 1550. Pope Julius III reigned over the papal court, entirely at the mercy of his young lover. In one of his first undertakings as pope, the besotted Julius rewarded the uneducated and socially awkward Innocenzo with a cardinal’s hat.

Although Vatican records claim that the pope and the cardinal were just friends, other sources reveal that Julius and Innocenzo shared a bed. It would have been one thing if Innocenzo was actually good at his job, but he wasn’t. He was so incompetent that Julius gave him a position at the papal court with no responsibilities. Julius’ relationship with the cardinal made him the laughingstock of Europe. Ambassadors, kings, and cardinals alike made fun of the pope and his illiterate lover. The pope’s famous love affair with the street urchin inspired the epic poem, “In Praise of Sodomy and Pederasty,” published with Julius’ blessing.

11. Pius II Wrote Pornography

Born into the Italian elite, Enea Piccolomini’s early life was anything but what his regnal name indicates. Before he took holy orders, he traveled to Europe as a representative of the Church, enjoying the pleasures of life. Cardinal Albergati, the papal legate of Pope Eugenius IV, sent Piccolomini to King James I’s court in Scotland to push the king into a ceasefire that would end the Hundred Years’ War. The trip permanently damaged Piccolomini’s health, but that did not stop him from indulging in women. He fathered illegitimate children with two mistresses, during his assignments in Scotland and Strasbourg.

An accomplished writer, Piccolomini lived at the court of King Frederick III of Germany as the monarch’s poet laureate. In 1444, he wrote The Tale of Two Lovers, which became one of the most popular books in the fifteenth century. The work is one of the first epistolary novels, centering on the exchange of letters between a servant and his married lover. With multiple references to erotic imagery, The Tale of Two Lovers is the medieval equivalent to today’s erotic novels. By the time of its publication, Piccolomini acknowledged several illegitimate children by his many mistresses.

To his credit, Piccolomini turned away from his former life after his election as Pope Pius II in 1458. Becoming a faithful servant of the morality of the Church, he openly criticized members of the College of Cardinals who ignored their vows of celibacy. In June 1460, Pius wrote a scathing letter to his Vice-Chancellor of the Church, Rodrigo Borgia, the future Alexander VI. Upon learning of Borgia’s preference for orgies and prostitutes, the pope chastised Borgia, claiming that a “Cardinal should be beyond reproach.”

10. Paul II Supposedly Died in Bed with a Page Boy

As the successor of the politically active Pius II, Pope Paul II’s only real success was introducing the printing press to Rome. He was vain and selfish, obsessed with his own good looks, although surviving images depict him as the opposite. A lover of appearances and grand display, Paul splurged on fancy clothing and an elegant tiara designed with sapphires, pearls, and diamonds. Ridiculed for wearing blush on his cheeks during public outings, Paul II was widely rumored to be homosexual.

Throughout his pontificate, stories and humorous poems circulated Rome that the pope loved two things: beautiful clothes and gorgeous men. The only thing that Paul loved more than his companions was melons. His favorite food appeared at every meal, and he often ate them until they made him sick. Before his death in 1471, rumors claimed that the pope liked to watch the torture of young boys while devouring a whole table of melons. Although the story is probably false, it didn’t help his reputation.

Paul’s papacy was unimpressive, and no one really noticed when he died. Pope Paul II’s official cause of death listed a heart attack after indulging in too many melons. This report is believable, given his fondness for him. However, another story claims that the pope died in bed with a page boy. As the servant sodomized him, the corpulent Paul’s heart gave out from the excitement. This story is also most likely false, but it has continued for over five hundred years.

9. Sixtus IV’s Nephew Was Also His Lover

During the Renaissance, popes appointed friends and family members to important posts in the Church to surround themselves with loyal followers. Cardinal Francesco della Rovere, elected Pope Sixtus IV in 1471, took nepotism to a completely higher level. Throughout his pontificate, Sixtus surrounded himself with handsome men. He appointed twenty-three cardinals, most of whom were young, attractive clergymen. He reportedly had a habit of rewarding his lovers and one-night stands with a cardinal’s hat.

However, it was Sixtus’ relationship with his nephew, Pietro Riario, that made heads turn. Pietro’s parentage became the subject of much debate: the son of the pope’s sister, many gossipmongers assumed that Sixtus had fathered the child himself. Regardless of Riario’s paternity, the pope took his nephew as his lover, spoiling the vain Pietro with land and wealth. He lived one of the most extravagant lifestyles in Rome, funded by the papal treasury. When Pietro died, he left the papacy in so much debt that Sixtus had to raise taxes and sell offices to the highest bidder.

Although historians make much of Sixtus’ homosexuality, he was actually bisexual. He had six illegitimate children, whom he also provided for with papal money. The Church soon ran out of funds: Sixtus established taxes on prostitution, and he penalized priests and cardinals for having mistresses. After passing these taxes, the pope continued to take male lovers. Sixtus’ romping sex life didn’t affect his legacy. Upon his death in 1484, no one cared who he took into his bed. Something reprehensible darkened his memory: he signed the papal bull that authorized the Spanish Inquisition.

8. Julius II, “The Warrior Pope,” Had Syphilitic Scars

Julius II, the “Warrior Pope” who conquered parts of Italy to add to papal holdings, dedicated his life to making the Church a secular power. In his distaste for his predecessor, Julius took a moral stand against Alexander VI, but he didn’t have a leg to stand on regarding sexual relations. Julius also conveniently bypassed the celibacy vow, fathering three daughters before he took the papacy. Like his uncle, Sixtus IV, Julius was most likely bisexual. Rumors of his attraction to men persisted throughout his pontificate, although there isn’t much evidence to confirm or deny his activities.

Accused of frequenting the male prostitutes of Rome, Julius’ fondness for his close associates opened him up to ridicule. The pope hauled the governor of Bologna to Rome to answer accusations of corruption and to beg Julius’ forgiveness. The ordinarily intransigent pope buckled in the presence of the governor, indicating to witnesses and the public, that Julius had romantic feelings – or at least an attraction – to the man. Upon the murder of one of his closest companions, Cardinal Alidosi, Julius grieved horrendously; he barricaded himself in his rooms, and he refused to eat. After he emerged, the pope traveled from Ravenna to Rimini in a closed litter, from which passers-by could hear the pope sobbing.

After a famous spat with Julius, King Louis XII of France called the Fifth Council of the Lateran to check the pope’s power. However, the council really gathered religious officials intent on deposing Julius. At the meeting, Louis’ supporters shamed Julius as a sodomite, declaring that ulcers covered the pope’s skin from complications of syphilis. This particular accusation seems to be true. On Good Friday in 1508, the pope refused to let the people of Rome kiss his feet because of the painful lesions on them.

7. Leo X Charged the Public for their Transgressions While Flaunting His Lovers

When Innocent VIII married his son to Lorenzo de Medici’s daughter, the latter secured a cardinal’s hat for his son, Giovanni. When his son left for Rome, Lorenzo warned him that it would be difficult to live a virtuous lifestyle in the city. Giovanni didn’t heed the advice: he had numerous affairs with men, well into his reign as the first Medici pope, Leo X. He chose handsome page boys to wait on him, and his sexual appetite resulted in a string of one-night stands across the city.

Leo’s predecessor Julius II bankrupted the papal treasury on conquering land and decorating the Vatican. To raise funds, the pope forced the public to pay fines for transgressions such as incest, premarital sex, and sodomy. While the people of Rome paid for their sins, Leo X openly flaunted his favorite lover, the singer Solimondo, at the papal court. When the people of Rome resisted paying the taxes, the pope threatened them, claiming that they would languish in purgatory – or worse – if they did not pay the fines.

When a measure came forward in the curia to pass a papal bull to limit the number of boys that cardinals kept as their lovers, Leo vetoed the motion. The pope’s behavior only increased the discontent with the Catholic Church across Europe; four years before Leo’s death, the German monk Martin Luther wrote his “95 Theses,” condemning the practice of selling indulgences for the forgiveness of one’s sins. The document kickstarted the Protestant Reformation, challenging the widespread corruption of the Catholic Church.

6. Sergius III Took His Cousin’s 15-year-old Daughter as His Mistress

At the beginning of the tenth century, a period known as the saeculum obscurum, the nobleman Theophylactus and his wife Theodora ruled the city of Rome. The papacy had no real power under the influence of the elite Theophylacti family. In 904, the ruler’s cousin Sergius invaded with an army, murdering anyone who stood in his path. With the power of the noble family and his soldiers behind him, he took control of the papacy, electing himself Pope Sergius III.

With such a violent beginning to his pontificate, Sergius shouldn’t have been surprised when two pretenders, the Antipope Christopher and Leo V, challenged him for the papal seat. The ruthless pope arrested them and executed them. After dispatching his enemies, the former nobleman embraced the trappings of wealth and power that came with his new position. Sergius frequently indulged in prostitutes, and his cardinals whispered that the pope was “the slave of every vice.” Just because he was pope didn’t mean he couldn’t have a little fun.

As if prostitutes in the Lateran Palace wasn’t shocking enough, the pope took his cousin’s fifteen-year-old daughter, Marozia, as his lover. In his late forties, the pope was thirty years older than her. Marozia gave birth to a son, who would later become pope himself, John XI. Despite his young mistress, Sergius continued to indulge in sexual excess until his death in 911. Later nineteenth-century Protestant historians ridiculed his reign, naming it “The Pornocracy.”

5. The Husband of John X’s Lover Elected Him Pope

John X’s sex life would eventually lead to his downfall. When he was still a priest, Giovanni da Tossignano had an affair with Theodora, the wife of Theophylactus. Whether or not Theophylactus knew that his wife was sleeping with the family priest, Theodora pushed her husband to appoint her lover as the Archbishop of Bologna in 905. If the nobleman did know, it didn’t seem to bother him: Theophylactus elected Giovanni as Pope John X in 914. When Theodora died two years later, her daughter Marozia, the former mistress of Sergius III, took her mother’s place in politics, and supposedly, in John’s bed.

Rumors that Marozia was also John’s lover probably aren’t true, for her enemies recorded them as fact. John X reached unprecedented influence for a pope of the period. After the death of Theophylactus, he lost his influential friends. To curb John’s power, Marozia married Guy of Tuscany, and the couple invaded Rome in 927. Resentful of his relationship with her mother, Marozia arrested John and threw him in the fortress prison, the Castel Sant’Angelo. John X’s death one year later may have been the result of the prison’s conditions, but it is more likely that Marozia and Guy executed him.

4. John XII Died in His Mistress’s Bed

After the death of John X, Marozia seized control of Rome and the papacy. She installed three puppet popes, including her son, John XI. Fed up with her antics, her other son, Alberic II, imprisoned her, and he took control of the city. On his deathbed in 954, he gathered the clergy and the nobility, convincing them to support his illegitimate son, Octavianus, as the next pope. The following year, Octavianus was elected Pope John XII.

In his first years as pope, the people of Rome accused John XII of incest, murder, and rape. John used the papal treasury as his personal spending account to finance his many vices. He indulged in the city’s prostitutes, housing many of them in the Lateran Palace for his own pleasure. When he wasn’t in his brothel, John seduced Roman widows and kidnapped female pilgrims on their way to St. Peter’s Basilica. As stories of his inclinations spread throughout Europe, the number of women traveling on pilgrimage significantly decreased.

The pope was a man ruled by his passions. Lavishing wealth and power on one of his mistresses, he made her governor of Rome. No woman was safe from John’s lust. When he seduced his father’s long-time mistress, she became pregnant, and she bled to death during childbirth. After almost a decade of his sexual antics, Pope John XII died in the bed of his latest mistress. Although the Church records state that he died of a stroke, other sources claim that the woman’s husband broke into the room and caught the lovers together. The cuckolded husband beat John to death in a jealous rage.

3. Alexander VI’s Love For Orgies and His Illegitimate Children Defined His Papacy

Born Rodrigo Borgia, the late-fifteenth century Pope Alexander VI enjoyed a long career as Vice-Chancellor of the Church before he bullied and bribed the curia into electing him in 1492. He was notoriously corrupt, selling indulgences and offices to enhance his own wealth. Highly regarded for his good looks and charm, Rodrigo fascinated both men and women. With his wealth and power came the attention of women; Rodrigo was no stranger to sexual liaisons, fathering several children before he became pope.

In 1460, Borgia attended an orgy, for which Pope Pius II wrote a stern letter, admonishing his behavior, even though the pope was no angel himself. Rodrigos’ favorite mistress, Vannozza dei Catanei, a member of a minor noble family in Rome, gave birth to four of his eight (perhaps more) children – Cesare, Juan, Lucrezia, and Gioffre. Although Vannozza remained his mistress for over twenty years, he cast her aside in favor of the beautiful Giulia Farnese, the teenaged daughter-in-law of his cousin. Despite his numerous affairs, Alexander’s children by Vannozza would play front and center throughout his papacy.

Arranging diplomatic marriages for his children to enhance his political power, Alexander’s notoriety grew as one of the most morally corrupt popes in the history of the papacy. His children’s reputations didn’t fare much better: his son Cesare, a Cardinal himself, fathered eleven illegitimate children, and Lucrezia had multiple affairs during her third marriage to Alfonso d’Este. In 1501, the Vatican’s Master of Ceremonies, Johannes Burchard, recorded an example of Alexander’s sexual appetites. At a sex party known as the “Joust of Whores,” the pope – accompanied by his children Lucrezia and Cesare – watched as fifty prostitutes stripped in front of him. Given his history with women, whether or not he solicited their services afterwards is up for debate.

2. Benedict IX Liked the Occasional Bestiality Session to Spice Up His Sex Life

At only twenty years old, the election of Pope Benedict IX in 1032 elected one of the youngest popes to the throne of St. Peter. Already a wealthy man through the patronage of his two uncles, Pope Benedict VIII and Pope John XIX, Benedict IX’s father bought his papal crown, appointing an immature, licentious youth to the throne of St. Peter. Benedict IX’s sexual antics became the scandal of eleventh century Rome. You can’t be called “a demon from hell in the disguise of a priest” if you don’t engage in a little sinful behavior.

In addition to seducing young boys in the Lateran Palace, his contemporaries accused him of theft, rape, and murder. To spice things up, Benedict enjoyed orgies and bestiality sessions. The Romans tolerated him for twelve years before they exiled him from the city in 1044. Two months into the reign of his successor, Benedict returned to Rome. In the only example of the same man serving as pope more than once throughout history, Benedict excommunicated his replacement and took back the papacy, starting his second pontificate with as much sexual debauchery as the first.

By May 1045, the city of Rome hated the pope so much that he sold the papal chair to his godfather, who took the name Pope Gregory VI. Benedict retired from religious life, marrying his cousin. Two years later, the restless Benedict launched yet another return to the papacy. The people of Rome had enough of the pope’s antics the third time around, the memories of his first two terms recalling the “Pornocracy” of previous years. The population exiled him from the city permanently. One of Benedict’s successors, Pope Victor III criticized Benedict “as a pope was so vile, so foul, so execrable, that I shudder to think of it.”

1. The Bisexual Boniface VIII Took Male Lovers and Had a Threesome with a Mother and Daughter

Boniface VIII’s papacy was so brutal and scandalous that it was immortalized in classic literature. In 1294, he badgered his predecessor, the morally infallible Celestine V, into resigning; after his election, Boniface threw Celestine into prison, where he died less than a year later. Known for his volatile temper, Boniface bullied Rome and the powers of Europe into acknowledging his authority in both religious and secular matters. If they refused to comply, he burned their cities to the ground.

The pope’s open view of sexuality made him the talk of medieval Europe. The bisexual Boniface liked to seduce young boys, allegedly declaring that sodomy “was no more a sin than rubbing your hands together.” Two of his male lovers publicly quarreled on the streets of Rome, fighting over which one the pope loved more and who received the finer gifts. Most importantly, they argued over which one of them had the right to call himself “the Pope’s whore.”

Pope Boniface VIII did enjoy some dalliances with women, so much so that he had two at one time. He reportedly had regular ménage-a-trois sessions with a mother and a daughter. According to his contemporaries, the pope broke the cardinal sins of incest and adultery and violated his vow of celibacy, all in one turn. After his death in 1303, the result of a kidnapping and beating by his enemies, Boniface’s name endured for his appearance in Dante Alighieri’s The Divine Comedy. As shocking as the pope’s sexual escapades were to medieval society, the author condemned him to the eighth circle of Hell for simony.

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