This year marks the 700th anniversary of the death of Dante Alighieri, one of the great authors of Western civilization. A mind formed in the Middle Ages might seem to have little to say to us today, but Dante’s magnificent mix of the traditions of antiquity, Christianity, and medievalism make him an ideal companion especially in our enlightened, secular age. One outstanding example of his enduring relevance is in his portrayal of liberty—and its absence—in Inferno, the first canticle of his Divine Comedy.

We think of liberty today primarily in a political register. To be free is to live in a republic, to vote, speak freely, assemble freely, and so on. But there is another form of liberty that is equally important, which focuses on how an individual exercises his free will and judgment. At first glance, since we are all equally endowed with free will and the ability to judge freely, we must all be equally free. But even in the 14th century this was a misconception that Dante sought to correct. Dante argues that judgment consists in knowing and pursuing the good. Those who err in either respect are not free. Every sinner in Hell has judged incorrectly and has therefore impaired his freedom in some way.

Liberty is a cornerstone of The Divine Comedy. “He’s in search of liberty,” Virgil says of Dante in Purgatory. And in Paradise, where man is truly free, we see liberty closely tied to motion and God’s love. But before Dante can ascend to God, he must descend into Hell. He must see what it means to be deprived of God’s love and the manifold ways we can be enslaved. He must understand that liberty is possible only with order. Every sinner in Hell is an example of a life without order. Dante’s encounter with these very human sinners shows him how evil can assume many different forms, how sins beget sins, and how easily we can reject liberty without even knowing it.

Hell is rigidly ordered in accordance with God’s will, consisting of nine circles divided into three broad types of evil, listed in order of increasing severity: incontinence, violence, and deceit. It is important to note that the punishments meted out in Hell are less divine vengeance than they are the inevitable outcome of the way the sinners lived their lives. They freely chose to do this to themselves. Their punishment in Hell—the contrapasso—is the logical extension of what they were doing in life. A sinner on earth who fails to repent and change his ways is already living his own punishment. We need not subscribe to Dante’s religious worldview to acknowledge that our vices or insecurities can imprison and devour us.

The logical conclusion of a sinful life, a life without order, is Satan. Found in the final canto at the centre of the earth, Dante’s Satan is a far cry from the energetic Satan of Milton’s Paradise Lost. Dante’s Satan is defined by his immobility and passivity. His three mouths gnaw endlessly, while his bat-like wings keep the pit of Hell frozen. At the furthest point from God, Satan is purely mechanical, bereft of all liberty. He is a gigantic air conditioner. The epitome of slavery, he is unable even to exercise God’s gift of speech. Dante and Virgil’s only interaction with him is to use his shaggy satyr legs as a ladder to exit Hell.

Most sinners are not so enslaved. Like most of us today, most are a mix of good and evil. Many of them may even know the good but fail to pursue it due to their weak will. They are placed in the upper circles of Hell, among the incontinent. Incontinence includes such sins as lust, gluttony, avarice, prodigality, wrath, and sloth. Because the incontinent subordinate their judgment to their desires, because they subordinate what is higher in man to what is lower, they are not free.

More odious to God are sins of violence, punished in circle seven. The violent are like beasts, unable or unwilling to use reason. Like the incontinent, the violent let their desires dominate their judgment, but they are punished more severely because their sins are harmful to human community or nature. The suicides are some of the most visibly unfree sinners because their very inability to deal with the life they have been given leads them to annihilate their liberty entirely. Consequently, they are trees, which, unlike humans, are unable to end their existence. They can speak only when one of their branches has been broken, i.e. once someone inflicts the harm of which they are no longer capable. In Canto XIII, Dante encounters Pier della Vigna, an advisor to Emperor Frederick II. He is brought down by the other jealous courtiers who stoke the Emperor’s suspicions of him. Blinded and thrown into prison, the disgraced advisor cannot bear hearing his reputation destroyed outside his prison walls, so he smashes his head against the wall. Much as with the other suicides, his interest in himself is intense. “My mind, in scornful temper, / hoping by dying to escape from scorn, / made me, though just, against myself unjust.” Pier della Vigna’s twisted syntax reflects his convoluted self-justification.

He is one of many examples of sinners who sense why they are in Hell but hold someone else to blame. The most famous example of this is Francesca da Rimini in Canto V. Francesca had been married to Paolo Malatesta’s deformed brother Gianciotto. She and Paolo fell in love as they were reading of Lancelot and Guinevere. Gianciotto found them in bed together and killed them both. For this treacherous act Gianciotto is in the ninth circle of Hell, but Paolo and Francesca are also guilty, which we are wont to forget amidst the seductive appeal of Francesca’s speech. For Francesca, the great culprit in her sin was the same force that still plays a commanding role in how we view so much of human relations today: love. “Love, quick to kindle in the gentle heart, / seized this man with the fair form taken from me. / The way of it afflicts me still. / Love, which absolves no one beloved from loving, / seized me so strongly with his charm that, / as you see, it has not left me yet. / Love brought us to one death.” This is not God’s love, which leads us to recognize our free will and aim at the good. Francesca’s love is beautiful but deceiving, for it causes us to suspend our judgment and abrogate our freedom by shifting responsibility for our actions to someone or something else.

But by far the worst sinners are those who break the bonds of human community through their deception. Dante condemns to circles eight and nine the fraudulent and the treacherous, those sinners who used their God-given capacity for speech and reason in order to deceive others. The severity of these sins is not to be underestimated; Dante spends half of the Inferno addressing the many ways in which people have deceived or betrayed one another. Dante and Virgil descend to circle eight on the back of Geryon, the personification of fraud, with the head of an honest man and the body of a serpent. Many of the fraudulent share in common that they prostituted someone or something for money. The pimps prostitute women; the simonists prostitute the Church (the bride of Christ); the soothsayers prostitute the mind of God; the barrators prostitute the state. Unlike Francesca, who holds love responsible for her sins, many of the fraudulent seem either unaware or unconcerned that what they are doing is wrong. They are unfree because they do not bother to judge between right and wrong.

Yet even among the fraudulent, there are souls whose sins are more ambiguous. In Canto XXVII, we encounter Guido da Montefeltro, whose opening exchange with Dante about the political situation in Romagna indicates that even in Hell he remains a prisoner of the petty politics above. Guido would be the quintessential Machiavellian if he did not seek to make amends for his earlier warlike ways by becoming a friar. But it is not for this that he finds himself in Hell. Like Francesca, Guido blames Pope Boniface VIII for reverting him to his earlier political ways. The Pope, who will take his place among the simonists, promised to absolve Guido of his sins if he would advise him how to conquer Praeneste. Guido advised him to “promise much with scant observance.” At Guido’s death, instead of Saint Francis, a black cherub claimed his soul. Although Guido had secured all of the external signs of salvation, internally he had not repented. He counselled the Pope to use deception, and he deceived himself into thinking that absolution would be enough to save his soul. He is too clever by half and a prisoner of his own deception.

But most ambiguous and instructive is Ulysses in Canto XXVI. Unlike many great pagans who are in Limbo, free of punishment but also of hope, Ulysses is placed in the eighth circle of Hell. Yet even there he is dignified and addressed with reverence. He relates how he and his shipmates, “grown old and slow,” sailed beyond the ends of the earth (the Straits of Gibraltar) when a whirlwind capsized their ship. On the surface, there is nothing particularly objectionable about Ulysses’ tale. By contrast, his actions prior to that point were the definition of deceit, such as persuading Agamemnon to sacrifice his daughter Iphigenia, stealing the Palladium, or devising the stratagem of the Trojan Horse. But Dante chooses not to focus on these earlier acts of deception, and he even depicts some of Ulysses’ good qualities. Much like Dante the pilgrim, Ulysses wishes “to gain experience of the world / and learn about man’s vices, and his worth.” Finally, like Dante himself, Ulysses is a great orator: “‘Consider how your souls were sown: / you were not made to live like brutes or beasts, / but to pursue virtue and knowledge.’ / With this brief speech I had my companions / so ardent for the journey / I could scarce have held them back.”

In Ulysses Dante sees himself and the potential dangers even in the pursuit of the good. Ulysses’ example is particularly illuminating because he seems to be both noble and free. He seems so close to judging rightly. Unlike many of the fraudulent, Ulysses does not pursue base ends such as wealth. He employs the highest means—speech and reason—to persuade others to pursue some of the highest ends—virtue and knowledge. But he does so without any sense of limits. Like a modern day globetrotter, Ulysses visits many exotic locations under the pretence of gaining experience of the world, but what does he actually learn? His aimless traveling does little apart from fueling his desire to see more. He loves discovering new things, just as he, Francesca, and Guido all love discovering new ways of deceiving themselves.

Herein lies the essential difference between Ulysses’ journey and Dante’s journey. Ulysses’ journey takes him outward, forever exploring everything but himself and his own faults. Dante’s journey takes him inward, to examine himself and his faults, to understand the divine order of Hell (and Purgatory and Paradise) in order to know true liberty. Dante’s pursuit of virtue and knowledge is circumscribed by this order. Ulysses has no such ordering principle. He represents liberty without order, which is all the more dangerous for offering the appearance of true liberty. In his hands, oratorical skill can be a great danger. It is revealing that Ulysses never builds communities but only ever destroys them.

When Ulysses’ ship was swept under by a whirlwind, “as pleased Another,” he was in sight of Mount Purgatory. He did not know it, but liberty and salvation were right in front of him. He was just looking in the wrong place.