10. Pope Boniface VIII (c. 1235 – 1303)
Born to a minor noble family in Anagni,
Italy, Benedetto Caetani became a
successful student of canon law and later a
member of the Roman Curia, eventually
winning the position of cardinal priest in
1291. He was elected Pope Boniface VIII on
December 24, 1294 after the pious yet
incompetent Pope Celestine V abdicated
(possibly due to Boniface’s own insistence).
One of his first decisions as pope was to
sentence Celestine to prison in the Castle of Fumone, where the old man was mistreated and eventually died ten months later. Boniface quickly became one of the church’s strongest advocates for papal supremacy in both spiritual and civil matters, involving himself in foreign affairs to no end. His desire for political domination, of course, did not sit well with many rulers of the day, such as Philip IV of France, whose policies of
clerical taxation angered the pope and prompted a string of bulls culminating in the famous Unam Sanctam, which essentially claimed all civil and spiritual authority for the papacy.
Other famous clashes include Boniface’s feud with the powerful Colonna family, which led to several of their towns being demolished – Palestrina, for example, was razed to the ground and 6,000 citizens were killed. In addition, Boniface aroused the anger of Dante Alighieri, whose portrayal of the pope
in his Inferno is anything but kindly, since he places Boniface in the eighth circle of his imaginary hell.
Boniface never quite attained to the absolute power he craved. Not surprisingly, his insatiable ambition led directly to a brutal beating at the hands of those who refused to submit to him, and within a month of this incident he was dead.

9. Pope Leo X (1475 – 1521)
Often associated with Martin Luther and the
upheavals of the Protestant Reformation,
Pope Leo X is also well-known for being one of the most lavish, uncontrollable spenders who ever headed the Christian church. A famous phrase attributed to Leo aptly illustrates his greatest priority: “Since God has given us the papacy, let us enjoy it.” According to Alexandre Dumas, “Christianity assumed a pagan character” as Leo doggedly pursued worldly pleasures.
Born Giovanni di Lorenzo de Medici, Leo
came from a powerful family and enjoyed
early favors that helped him acquire the
papal throne by the time he was 37. A
patron of the arts, education, and charity,
Leo certainly deserves to be recognized for
elevating the church’s status, but his
preference for money and political
advancement rapidly exhausted the
treasury. So financially unstable did his
position become that he was eventually
forced to pawn off furniture, jewels, and
statues from the palace, as well as borrow
huge sums of money from creditors (who
were ultimately ruined when he died).
In addition to living a life of splendor, Leo
practiced nepotism, famously used the sale
of indulgences to finance the reconstruction
of St. Peter’s Basilica, and was even accused of homosexuality. In fact, some sources hold that he died in bed while getting it on with a youth. That accusation may or may not be true, of course, but one thing is for sure: Leo certainly let his love of luxury get the best of him.

8. Pope Clement VI (1291 – 1352)
Pierre Roger, a Frenchman, was the fourth
of the Avignon popes, and took the name
Clement VI for his pontificate. He was not a
particularly evil man; in fact, his efforts
during the Black Plague did much to provide refuge for the Jews, who automatically became the scapegoats for the deadly breakout. Described as a fine gentleman, a prince, and a patron of the arts and learning, Clement lacked one important characteristic that is rightly expected of popes – saintliness.
By his own words, Clement was “a sinner
among sinners.” His love for expensive
living quickly drained the savings of his
frugal predecessor (Benedict XII), and
Clement resorted to raising taxes and selling off bishoprics to finance his worldly pursuits. Throw in a little nepotism to boot, and you’ve got yourself a pope who may very well have been a man of decent character, but who also used his powerful position for his own sexual adventures, cheerful pleasures, and overall celebration of the world’s many vices.

7. Pope Urban II (ca. 1035 – 1099)
It’s undeniable that Otho de Lagery, who
became Pope Urban II in 1088, was a
talented diplomat and successful leader,
responsible for establishing the modern
Roman Curia and supporting reforms of the
clergy. What he is most often remembered
for, however, is his unfortunate role in
launching a bloody holy war against Muslims that has since come to be known as The First Crusade.
In 1095, Byzantine Emperor Alexios I
requested Urban’s aid in fighting off the
Turks, who had conquered most of Anatolia. Urban responded favorably by using his remarkable rhetorical skills to preach “Just War” – a holy, God-ordained crusade to liberate the eastern churches and the Holy Land from Muslim rule. By appealing to Catholic anger over the rumored (and often unfairly trumped-up) atrocities committed by the invading Turks, and by guaranteeing remission of sins to those who would participate in the fight, Urban was able to organize a large-scale uprising of piously outraged soldiers of Christ. The religiously-sanctioned First Crusade, while successful in defeating Muslim forces in Anatolia and the Holy Land, was very costly in terms of casualties. Not only was there a huge loss of lives on both sides, but the horrible offenses committed by enraged Christians against Jews, Muslims, and even members of the “schismatic” Eastern church will always be a bloody stain on the pages of
church history.

6. Pope Julius III (1487 – 1555)
Born to a famous Roman jurist, Giovanni
Maria Ciocchi del Monte was elected pope in
1550 as a compromise candidate, and chose
the title Julius III. While his early career in
the church shows that he was very capable
and successful, his papacy is known for
being extremely ineffective and
undistinguished. For the most part, Julius
withdrew to his palace and spent the
majority of his time seeing to his own
personal pleasures and keeping out of
political affairs.

However, it was his relationship with a boy
named Innocenzo that tarnished his name
more than anything. Julius discovered
Innocenzo as a young beggar in Parma
before ascending to the pontificate, and he
adopted him as his own nephew. When Julius
became pope, he elevated Innocenzo to the
status of cardinal-nephew and bestowed
many gifts and benefices upon him. In fact,
the relationship between Julius and
Innocenzo showed signs of being much more
intimate than normal family ties, and many
reports indicate that Julius actually had an
extended sexual affair with the young man.

5. Pope Stephen VI (? – 897)

Little is known about Pope Stephen VI’s
personal life and background, although he
was a Roman and the son of a priest named
John. The reason his name stands out in
church history is because of his involvement
in what is perhaps the most bizarre
ecclesiastical trial of all time – the Cadaver
Synod of January 897.
As the name reveals, this grotesque synod
was convened to put a corpse on trial.
Stephen ordered it for the sole purpose of
passing judgment on the freshly-exhumed
body of Formosus, who had held the papacy
from 891-96. Due to activities in Bulgaria
which compromised his duties as bishop of
Porto, Formosus had been excommunicated
by then-pope John VIII (872-882), but after
John VIII’s death he had reassumed his
bishopric in Porto and was elected pope in
891.
Political interests regarding rightful claims to
the throne of the Holy Roman Emperor
resulted in animosities that created a trickle-
down effect and impacted later popes.
Stephen VI and the Cadaver Synod are the
most famous instance of reactions to Pope
Formosus.
While it is not perfectly clear who exactly
instigated the trial, the fact of the matter is
that Stephen ordered Formosus’s body to be
disinterred and seated on a throne in the
Basilica of St. John Lateran in Rome. A
deacon stood next to it to act as its
spokesman while Stephen lambasted it with
accusations.
The corpse was condemned for
transmigrating sees, committing perjury,
and acting as bishop after being deposed. As
punishment, his body was stripped of its
vestments, the three fingers of the right
hand used for benedictions were cut off, and
all his former ordinations were declared null.
The body was then buried, exhumed again,
and finally thrown into the Tiber River.

4. Pope Sergius III (? – 911)
The son of a Roman noble and a member of
the ultimately unsuccessful faction which
opposed the policies of Pope Formosus,
Sergius III must chiefly be understood
through the biased writings of his enemies,
since almost all sympathetic accounts have
been destroyed.
Nevertheless, what we do have on Sergius
suggests that he didn’t quite measure up to
Christian standards for piety. He was
accused of ordering the murders of his
predecessor Pope Leo V and Antipope
Christopher in prison. It is said that his
mistress was the young Marozia (later to
become a powerful Roman noblewoman),
and it was their son who became Pope John
XI in 931.
It gets weirder, though. Pope Stephen VI’s
infamous Cadaver Synod had been declared
void by succeeding popes, but when Sergius
came to power, he voiced his displeasure
with Formosus by annulling all of his
recently reinstated ordinations. There is
even a report that Sergius had the corpse of
Formosus exhumed, tried, beheaded, and
thrown into the Tiber – all over again!

3. Pope Benedict IX (c. 1012 – 1065/85)
Benedict IX, born Theophylactus of
Tusculum, is known mainly for two things:
1) he held office on three separate
occasions, and 2) he is the only pope who
ever sold the papacy (to his own godfather,
of all people).
Benedict became pontiff at a very young
age, thanks to the political prowess of his
father, who had managed to get the papacy
reserved ahead of time for his son. With
little actual training or preparation that
qualified him to act as pontiff, Benedict led a
highly immoral life, and was accused of
various rapes, adulteries, and murders.
According to St. Peter Damian, Benedict was
“a demon from hell in the disguise of a
priest,” and his carousing eventually caused
him to be forcefully expelled from Rome.
Benedict managed to regain his throne, but
then – surprise, surprise! – he was
sidetracked by a prospective marriage (to
his cousin) and sold the papal chair for a
significant amount of money to his
godfather, a priest who named himself Pope
Gregory VI. His later repentance and
attempt to resume his position created quite
a controversy, forcing the German King
Henry III to intervene. Benedict was
subsequently excommunicated from the
church.
“His life as a pope,” wrote Pope Victor III,
“was so vile, so foul, so execrable, that I shudder to think of it.”

2. Pope John XII (c. 937 – 964)
Born in Rome, the young Octavianus
practically had the papacy handed to him on
a silver platter. His father, a patrician of
Rome, made the Roman nobles swear an
oath that at the next vacancy in the papal
seat, Octavianus would be elected. Sure
enough, when he was only 18 the reigning
pope passed away, and Octavianus was
chosen as the successor, taking the name
Pope John XII.
Almost everything known about John XII is
found in the writings of his enemies, so it’s
possible that the accounts we have are
factually distorted. Nevertheless, the stories
we do have are quite shocking – he was
accused of committing many adulteries
(even with his own niece), turning the
Vatican into a whorehouse, blinding his
confessor, castrating and then murdering a
subdeacon, invoking demons and foreign
gods… the list goes on and on.
Even if some of the reports were falsified, it
still appears that John XII made for a pretty
bad pope. When we read the account of
John’s death that claims he was murdered by
a jealous husband whose wife was the object
of the pope’s special attention, it’s not too
hard to believe it.

1. Pope Alexander VI (1431 – 1503)
The reward for “Baddest Pope Ever”
arguably goes to Rodrigo Borgia, who
enjoyed the benefits of having an uncle who
just happened to be Pope Calixtus III.
Thanks to his convenient social status,
Borgia passed through the ranks of bishop,
cardinal, and vice-chancellor, gaining
enormous wealth along the way. In 1492, he
was actually able to buy his way into the
papacy, defeating two other opponents by
means of bribery.
Alexander was so corrupt that his surname
eventually became a byword representing
the hellishly low papal standards of the time.
He sired at least seven different illegitimate
children by his mistresses, and didn’t
hesitate to reward them with handsome
endowments at the church’s expense. When
low on finances, he either established new
bcardinals in return for payments, or he
slammed wealthy people with completely
fabricated charges, jailed or murdered them for said false charges, and then stole their
money.
Not surprisingly, there is very little about
Alexander VI that can be considered godly or
even lawful. His goals were selfish and
ambitious, and the orderly government he
initially administered quickly deteriorated
until the city of Rome was in a state of
complete disrepair. The words spoken by
Giovanni de Medici (the future Pope Leo X)
after Borgia’s election are telling:
“Now we are in the power of a wolf, the
most rapacious perhaps that this world has
ever seen. And if we do not flee, he will
inevitably devour us all.”

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