How or why is Dante sympathetic to some sinners and not others?

Dante is far more sympathetic to sinners who have committed smaller sins, like being ignorant of God or rejecting Church doctrine. He sympathizes with these people because although they did sin, they did not harm others in the process. Upon reaching the dwellings of those who committed fraud or violence, Dante feels little to no sympathy and judges the sinners. Virgil reminds Dante that only God can judge, and Dante should not imperil his soul by judging the other sinners. 

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Dante Alighieri (1265-1321) is an Italian poet who modeled The Divine Comedy after Virgil’s Aeneid in the form of an epic poem. It is separated into three distinct parts: the Inferno, or Hell, which is reserved for those who must suffer eternal damnation because they died in sin; the ...

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Dante Alighieri (1265-1321) is an Italian poet who modeled The Divine Comedy after Virgil’s Aeneid in the form of an epic poem. It is separated into three distinct parts: the Inferno, or Hell, which is reserved for those who must suffer eternal damnation because they died in sin; the Purgatorio, which is the place those who have repented their sins must wait before entry into Heaven; and Paradiso, the place enjoyed by those whose souls are pure and free from sin.

The author Dante is a religious man who believes that to enter Heaven a human being must understand the nature of sin. His epic poem represents a man’s journey to Hell in order to gain that understanding. The protagonist making the journey is aptly named Dante, but represents humankind. Readers are cognizant that the character Dante and the author Dante are different. They can still recognize that the author’s beliefs are infused into his fictional hero and protagonist.

The epic hero is guided through the Inferno by the Roman poet Virgil. Beatrice, Dante’s earthly love who now lives in Heaven, asks Virgil to help him. There are nine concentric circles of Hell forming a funnel, and each level goes deeper into the pit at the bottom. As Dante travels deeper into Hell, the sins of the souls suffering are more serious. Thus, the protagonist tends to be more sympathetic toward some at the top of the funnel because their sins are of a lesser magnitude.

As the journey begins, Dante has lost his way through life. He finds himself confused. He wants to travel the right path to God, but must first learn the nature of sin:

Midway upon the journey of our life
I found myself within a forest dark,
For the straightforward pathway had been lost.

When Dante arrives at the Gates of Hell, he is terrified by the sign above reading, “All hope abandon, ye who enter in!” When he and Virgil enter the first circle of Hell called Limbo, he identifies with the souls trapped there. They had not found Christianity. As pagans, they had lost hope and were doomed for eternity. He knows that he, too, is a lost soul and is sympathetic to that level of sinners:

And if they were before Christianity,
In the right manner they adored not God;
And among such as these am I myself.
For such defects, and not for other guilt,
Lost are we and are only so far punished,
That without hope we live on in desire.
Great grief seized on my heart when this I heard,
Because some people of much worthiness
I knew, who in that Limbo were suspended.

At the sixth level of Hell, Dante encounters those who have rejected Church doctrine. Once again, Dante is sympathetic to them since they have committed sins that were not harmful to others. Nevertheless, they burn in tombs of fire.

In the seventh circle of violence and the eighth circle of fraud, the traveler feels less sympathetic toward the sufferers. He learns that since violence harms others, the punishment is greater, but that God hates fraud, especially that committed against family, even more than violence because those who commit it misuse human reason. Fraud against family is punished in the ninth circle of Hell.

Upon entering the ninth circle where Lucifer resides, Dante no longer feels pity or sympathy for the sinners he sees. He develops an attitude of anger and contempt for them and wishes to escape their presence. He and his guide ascend through the funnel toward hope:

The Guide and I into that hidden road
Now entered, to return to the bright world;
And without care of having any rest
We mounted up, he first and I the second,
Till I beheld through a round aperture
Some of the beauteous things that Heaven doth bear;
Thence we came forth to rebehold the stars.”

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For Dante, there are gradations of sin; some sins are more serious than others. Additionally, some sinners are more worthy of sympathy than others. The Divine Comedy is an intensely religious work, a work of vision and prophecy. In writing his masterwork, Dante wants us to realize that the ultimate ground of our being is God. In order to find God, we must detach ourselves from the things of the temporal, finite world, look within ourselves, and surrender to the light of the Empyrean as symbolized in the final cantos of the Paradiso.

God is the very foundation of our being; if we reject God, we reject ourselves and the truth of our very existence. In essence, sin is a failure to recognize this, and sin distances our being from the God that resides within us by forming too great an attachment to the ephemeral things of the spatiotemporal world: wealth, power, fame, and the pleasures of the flesh.

All of these things alienate us from our true selves, from God, and from the very depths of our own being. But some attachments lead us further astray than others. The adultery of Paolo and Francesca—the result of misreading a tale that was actually supposed to discourage adultery—is considered by Dante as much less serious than the sin of simony, the buying and selling of church offices, by the notoriously corrupt Pope Boniface VIII.

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Dante Alighieri's Divine Comedy begins with Inferno, an epic poem that shares Dante's journey through the nine circles of Hell. During the trip, Dante learns the many ways that souls are tortured in Hell: it ranges from Limbo, essentially a less ideal version of Heaven, to Treachery, where souls are trapped in ice, perpetually separated from God's love and warmth.

While Dante travels through the circles of Hell and encounters the damned souls, he often expresses sympathy for sinners he feels are unfairly punished for negligent misdeeds on Earth. When he witnesses the twisted forms of the human body in canto XX, Dante cries, and Virgil admonishes him for daring to question God's judgment. Later, in canto XIII, Dante offers compassion to the souls of suicide victims who are crying out for pity.

In other instances throughout the poem, Dante is devoid of empathy. He calls Filippo Argenti "so fallen and so foul" in canto VIII and later, when Argenti tries to grab Dante's boat, Dante says, "Down! Down! With the other dogs!" He creates his judgements on the actions of the sinners and the kinds of punishments they should receive, which are not always congruous with the punishments chosen by God. Virgil warns him that judging God is a sin and encourages Dante to protect his own soul by putting his judgmental thoughts aside.

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I like Dr. Fajardo-Acosta's (of  Creighton University) analysis, excerpted here (a link to the full lecture below):   

"Dante's love and sympathy for several of the souls in hell acts as a form of redemption for them (e.g. Paolo and Francesca in the circle of the lustful, Canto 5; Brunetto Latino in the circle of the sodomites, Seventh Circle, Canto 15)Dante re-evaluating each sin and each sinner, in many cases forgiving what the Church could not; humanizing the sinner and showing understanding and tolerance of human passions; Dante imitating Christ and his forgiving and redemption of humanity: allusion to legends of Christ entering hell after his death and rescuing a number of souls (Adam and Eve, the prophets, etc.)

Dante's mission is re-redemption of the world by recalling and imitating the love and mercy of Christ." 

As for Dante's lack of concern or anger towards certain sinners, Acosta addresses this as well:  problems of Dante seen in his wrath in the circle of the wrathful (Fifth Circle) when he is enraged at the sight of Filippo Argenti, a personal enemy; Dante feels no sympathy for Filippo's tears and suffering and even desires to see him suffer more (Virgil too is caught up in cruelty and desire for vengeance)problems of Dante especially visible in the Ninth Circle of hell, the frozen, circular lake of ice at the bottom of hell and the residence of Satan."

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