It was just outside the gates of Hell that Dante, along with his guide Virgil, encountered a throng of aimless souls doomed to wander for eternity.

In “The Divine Comedy,” the epic poem composed 700 years ago, the entrance to the underworld was clogged with the souls of people who had accomplished nothing in life. “These wretches, who never were alive, were naked, and much stung by gad-flies and by wasps that were there.”

Dante Alighieri’s eponymous narrator recognized one of the phantoms. “I saw and knew the shade of him who made, through cowardice, the great refusal,” he notes.

That unlucky soul went unnamed in the text, but most interpretations point to Pope Celestine V, born Pietro Angelerio, an intellectual hermit who became the Catholic pope in July of 1294 but retired five months later, citing a lack of physical strength and a desire to live a more peaceful life. For Dante, the resignation merited eternal damnation.

It is an ominous precedent for Pope Benedict XVI, who is also stepping down due to his physical inability to continue as the leader of the Roman Catholic Church.

Times have changed since the days of Celestine V, who resigned only to be captured by his successor and imprisoned in a castle until his death. Pope Benedict can expect to retire in relative peace, and will likely retain plenty of influence at the Vatican -- but questions will persist as to why he decided to give up his post.

After all, voluntary papal resignations are exceedingly rare. Nearly every pope has died in office; the last to retire alive was Gregory XII in 1415.

It is of course possible that Pope Benedict, 85, truly feels that the church deserves a more vigorous leader. But his sudden retirement could also have to do with a realization of ineptitude -- a taboo subject for many believers. Faced with the cloistered, tangled nature of Vatican politics, this pontiff was simply not the right man for the job.

“The problem was that Pope Benedict has always considered himself above politics, which makes sense for an intellectual like him,” says Massimo Faggioli, a Vatican expert and author who teaches theology at the University of St. Thomas. “But as the pope, you are the commander in chief. And in this, he has been reluctant.”

Holy Water

Benedict, the former Cardinal Joseph Ratzinger, announced his resignation in a brief speech on Monday morning, which he delivered in Latin.

“In today’s world, subject to so many rapid changes and shaken by questions of deep relevance for the life of faith, in order to govern the barque of St. Peter and proclaim the Gospel, both strength of mind and body are necessary, strength which in the last few months, has deteriorated in me to the extent that I have had to recognize my incapacity to adequately fulfill the ministry entrusted to me,” he said, as translated by the Vatican.

Benedict will step down on Feb. 28, and a group of 118 cardinals will be responsible for selecting the next head of the Catholic Church. A new pontiff task is expected to be chosen by this year’s Easter holiday, which falls on March 31.

That marks the end of a long road for Ratzinger, who was born in Germany and entered seminary as a teenager. He spent much of his young adult life in academia. There he gained a reputation as an intellectual, a perception reinforced by his quiet demeanor. Before becoming the pope, Ratzinger was devoted to his cats and liked to pass the time playing classical songs on his piano.

“Ratzinger was much more of a scholar and interested in theological questions,” said Frank Coppa, a professor at St. John’s University who has written extensively on the Roman Catholic papacy. “He really wanted to focus on theological issues in an abstract sort of way.”

Today, Benedict is widely known as a conservative theologian. But that wasn’t always the case; the young Ratzinger once leaned toward the left when it came to religious doctrine. During the 1960s, he was a theological consultant at the Second Vatican Council, a series of gatherings wherein high-ranking clerical officials revolutionized the very foundations of the church.

At the council gatherings, Catholic leaders made sweeping reforms in order to make the religion more accessible to global audiences. Masses no longer had to be held in Latin; Scripture was subject to looser interpretations; human rights and social justice were more forcefully championed.

But in later decades -- and finally as the leader of the church -- Pope Benedict disappointed liberals by making disparaging comments about Islam, opposing homosexuality and maintaining a hard line against contraception.

“Pope Benedict was seen as more progressive during the 1960s, but then he backtracked,” said Gerald P. Fogarty, a Jesuit priest and professor of religious studies and history at the University of Virginia. “I have a lot of sympathy for the pope in not knowing exactly what to say; even his own followers were divided.”

On top of all that, Benedict XVI had some big shoes to fill. Pope John Paul II was a beloved figure who increased the church’s outreach and appeal; when he died in 2005, some saw Ratzinger -- one of the oldest popes ever to take the helm -- as a mere placeholder. But as it happened, he presided over some very trying times.

The Confessional

The wall of secrecy that has long surrounded the Vatican’s inner workings came crumbling down last year when Pope Benedict’s own butler, Paolo Gabriele, released confidential documents and correspondences to an Italian journalist. The scandal -- dubbed Vatileaks -- exposed infighting and corruption among Vatican officials. In particular, the documents highlighted internal divisions over the outsized role played by Cardinal Tarcisio Bertone, who serves as the Cardinal Secretary of State.

The leaks made clear that Bertone, who has been staunchly defended by Benedict, was reviled by many of his colleagues due to his perceived mismanagement of Vatican finances and his brazen outspokenness, which was beginning to weigh on the reputation of the church.

Cardinal Bertone still retains his influential position, but that is unlikely to be the case following the resignation of Pope Benedict in a few weeks.

“The new pope can dispose of anybody who was a disservice,” said Faggioli. “It’s highly unlikely that Bertone will stay because he has been criticized unanimously and for a number of reasons.”

That’s good news -- but corruption is not the worst of the Vatican’s worries.

The Catholic Church has come under intense scrutiny in recent years for a deplorable history of sex crimes committed by clergy members. The problem goes back decades; since the 1950s, thousands of priests and officials in dioceses around the world have been accused of sexually abusing minors.

To his credit, Benedict was the first pope ever to meet publicly with victims of abuse. In fact, he played a major role in the controversy as early as 1981, when he was appointed to head the Congregation for the Doctrine of the Faith, which essentially put him in charge of Vatican investigations into clerical misconduct.

But Ratzinger was repeatedly accused of neglecting to fully investigate -- and even participating in -- cover-ups of abuse.

Pope Benedict scored one high-profile victory against sexual abuse in the case of Marcial Maciel, a powerful and well-connected Mexican priest with a knack for fundraising. Maciel had a long history of drug use and sexual abuse against children but seemed invincible until 2006 when, in the face of public outcry, Benedict punished the offender by removing him from active ministry. Maciel died in 2008.

But even then, critics charged that the action was far too little and much too late. They point out that even in his capacity as the leader of the  Congregation for the Doctrine of the Faith, Ratzinger presided over seemingly interminable delays in the prosecution of Maciel and other alleged offenders.

Last Rites

As Pope Benedict steps down, the many problems that plague the Catholic Church have yet to be resolved.

The next big question is whether the incoming pontiff can bring the necessary mix of moral integrity and political savvy to the post.

Benedict’s failures prove that intellect alone is not enough to exercise real power in the Vatican; it must be combined with a deep knowledge of the institution’s inner workings, something the outgoing pope lacked even though he had spent many years of his life mingling with top clergymen before becoming their leader.

It is important to note that Ratzinger was not Italian. Nor was his predecessor, who hailed from Poland. But before John Paul II, Italian popes had been the rule for over 400 years running.

“The Italians knew how to operate, and I would say things changed dramatically under John Paul II,” said Fogarty. “He didn’t really know how to work the Vatican, and I suspect this is still true for Pope Benedict.”

Vatican insiders could very well have an advantage over foreign papal candidates, and that’s bad news for Catholics around the world who are hoping to see some papal diversity this time around. There are eligible cardinals who hail from countries all over the world; such an appointment could do much for the global appeal of a struggling religion.

Whether he hails from Nigeria, Brazil, Canada or Italy, the next pontiff will have to strike that perfect balance between modernization and tradition, which the current incumbent never quite mastered -- a sweet spot that neither deters new acolytes nor alienates longtime believers.

And while his successor struggles with that, Benedict XVI plans to go back to a life of quiet reflection -- just what the former hermit Celestine V longed for as he wasted away in captivity.

“Let us entrust the Holy Church to the care of Our Supreme Pastor, Our Lord Jesus Christ, and implore his holy Mother Mary, so that she may assist the Cardinal Fathers with her maternal solicitude, in electing a new Supreme Pontiff,” said Pope Benedict on Monday.

“With regard to myself, I wish to also devotedly serve the Holy Church of God in the future through a life dedicated to prayer.”