During Dante's time (the turn of the fourteenth century), the Catholic Church was known for greed and corruption. Dante's depicted hell is a place where the punishments for sinners fit their earthly crimes, and so he imagines the punishments of several contemporary members of the Catholic clergy for their sins.

Dante considers premeditated sin of greed to be one of the highest levels of offense against God. Dante places Nicolas III upside down in a ditch in Hell for committing simony, the selling of Church indulgences. Dante later goes on to insinuate that Boniface VIII and Clement V deserve the same fate. Dante did not like Boniface personally, since Boniface was instrumental in Dante's exile from Florence. Dante saw Boniface as being greedy for secular power as well as spiritual.

Dante did not see piety in the Church; rather, he saw a group of people using the name of Christianity for their own motivations. Dante wrote his work partly as a great Italian epic. He also wrote it as a criticism of the world in which he lived. Dante saw the nepotism under Nicolas III and the greed of Boniface VIII as sins which used God's name for vile ends. Dante was not alone in finding faults with the Church at this time. Rather, what makes him remarkable is that he decided to imaginatively place popes in hell for their sins at a time when the papal office was supposed to be infallible.

The major distinction to keep in mind here is that in Christian theology there are really two churches. One is the ideal church which is the Christian community as it follows and embodies divine will, and the second is the church as a fallible human institution. The difference between the two is original sin, which ensures that all human acts and institutions are by their nature flawed. Thus, when Dante criticizes the Church, he is not being a radical opponent of the Church or anti-Christian, but rather participating in a traditional theological exercise of showing how the human Church necessarily fails to live up to its divine ideals due to human fallibility. The critique is not of the Church per se, but of the flawed humans who err in embodying a divine institution due to the inherently fallen nature of humanity. He thus condemns members of the clergy who do not live up to the ideals of the Church and Bible. This is exemplified by his dressing hypocrites in garb similar to that of Benedictine monks whose luxurious lifestyle was in direct opposition to their vows.

In Dante's period, the Church was notoriously corrupt and filled with scandals. One of the greatest objections Dante voices is that many of the clergy have fallen prey to the sin of avarice. Rather than living a life of poverty and renunciation, they live in great luxury. He also strongly condemns the practice of simony, the sale of church offices for money. He sees, quite accurately, that this leads to clergy who are not knowledgeable or pious; often the second and third sons of the wealthy purchase the office and then live luxuriously at the expense of the Church coffers (Inferno 19.1-4; 55-7; 106-11). He also displays some discomfort with the practice of selling indulgences.

Next, he objects to the interference of the Church in politics, believing that this lust for secular power corrupts the Church. Pope Nicholas is condemned to Hell for his territorial acquisitions as well as nepotism. Pope Clement V and the Avignon papacy are similarly condemned as examples of the Church seeking secular power.

One distinct way in which Dante criticizes the church is by placing specific members of the church in the most severe positions in the Inferno.  Dante is strict on the idea that institutional religion that loses its way is even worse than not having religious backgrounds. For example, the souls in limbo have failed to embrace a religious identity.  It is interesting to see Dante believe that sins of ignorance are not as bad as direct sins of knowledge.  In contrast to the church institution that condemned those who were not baptized, Dante takes a more lenient approach to the unbaptized.  Their crimes are not as bad as those who have lied in the name of the Church or have engaged in simony (Canto XIX.)  Dante's criticism of the church's practice of simony is blistering. He condemns Pope Nicholas III for his self- interested sale of holy items.  Pope Boniface VIII receives the same condemnation.  This feeds the theme that Dante has developed throughout the work:  Those in the position of power have a higher obligation and imperative to embody good and righteousness.  When they do not, their condemnation should be harsher and swifter than anything else.  People who use elevated positions in society- civil or sacred- receive the worst of punishments.

In a larger sense, Dante's premise as the pilgrim or "the wanderer" is a criticism of the Church.  The established condition of religion has left someone as spiritual as Dante out of its sights.  It is deliberate that Dante opens the work as one "in a dark wood."  In the progression through Hell, it is clear that part of the reason that Dante is lost is because he feels estranged from the institution of religion.  Formal religious structures have not embraced the individual who searches for meaning and understanding.  This becomes one of Dante's key criticism.  If there was a spiritual understanding of the needs of its congregants, perhaps Dante would not be as lost as he is.  The entire need to endure what he does is because traditional religion in the form of the Church has "lost its way" causing pilgrims like Dante to be in a "dark wood."  Dante's exploration is as much the failings of the Church as it is his own.