A Novel ~ The Imaginative Conservative

In taking his autobiographical protagonist through hell, Winston Brady does many things that would, I believe, have pleased Dante Alighieri. Like Dante’s “Inferno,” Brady’s “Inferno” tests the will and courage of its hero, forcing him to wrestle with his American identity and legacy, to understand the grave nature of sin, and to seek repentance from Christ.

The Inferno: A Novel, By Winston Brady (272 pages, Fidelis Publishing, 2023)

In Book XI of the Odyssey, Homer sends his hero on a journey through the underworld. Though the purported reason for his journey is to gain knowledge from the blind prophet Tiresias that will help him to return safely to Ithaca, most of what Tiresias tells him is repeated by Circe. The repetition suggests that there is a deeper reason that Odysseus must make his descent, a personal one that has more to do with facing his fears and testing his will than gaining information.

In Book VI of the Aeneid, Virgil, in imitation of Homer, sends his hero on a similar journey to the realm of the dead. Though Aeneas, too, receives information about what is to come, the true purpose for the journey is to help transform him from a Trojan into a Roman, from a survivor of a dead city to the builder of a city yet to be born. Like Odysseus, Aeneas is changed by his encounter with the underworld, but in a fuller way that involves his citizenship as a Roman.

In imitation of both Homer and Virgil, Dante sends his hero, who also happens to be himself, on a book-length journey through hell that forces him to confront, not only his personal will and courage and his Florentine citizenship, but the deceptive, deadly, soul-crushing power of sin. On his journey, Dante meets both mythical and historical figures who reveal to him the dangers of a life that is not bounded by the fear of God, that does not yield itself to the law of God, and that does not surrender itself to the love of God.

Buoyed by a heady mixture of literary bravado and deep spiritual humility, Winston Brady takes up the epic mantle of Homer, Virgil, and Dante to send his hero, the partly autobiographical Evan Esco, on a harrowing journey to hell and back. Like Dante’s Inferno, Brady’s Inferno tests the will and courage of its hero, forcing him to wrestle with his American identity and legacy, to understand the grave nature of sin, and to seek repentance from Christ.

Brady, the Director of Curriculum and Thales Press at Thales Academy, is a strong believer who is upfront about Christ, the gospel, and biblical theology and morality. Influenced as much by Pilgrim’s Progress, Paradise Lost, and Screwtape Letters as he is by Dante’s Inferno, Brady is crystal clear about the nature of sin and salvation, works and grace, and the book ends with a powerful gospel presentation. Although this may dissuade readers who do not like Christian fiction that is theologically on the nose, I urge such readers to give the novel a chance. Far from a thinly-disguised sermon, it offers a deep dive into the human soul, particularly the American soul, that will reward those who are willing to accompany Brady and Evan on their descent.


The depressed, alcoholic college student Evan Esco, whose name in Latin means “I disappear,” had hoped that by killing himself he would cease to exist and so bring an end to his pain and suffering. Instead, he wakes to find himself in hell, where his guide, Ernest Hemingway, tells him that he has been granted the privilege to tour hell (the inferno) and converse with some of its inmates, with the possibility that Evan will repent and escape eternal damnation. In taking his autobiographical protagonist through hell, Brady does many things that would, I believe, have pleased Dante: he conjures a realistic, terrifying geography for hell, partly by making running comparisons to earthly landscapes; he develops a strong rapport with his guide that develops and deepens over the course of the journey; he carefully marks his hero’s spiritual growth (Dante, by slowly hardening his heart against sin; Evan, by slowly grasping the full nature of repentance); he vindicates God’s justice while clarifying man’s responsibility; he creates memorable demons and punishments; and, he ranks sins in accordance with their ability to cut us off from God.

All these things Brady does well; however, the centerpiece of the book is the dialogues Evan has with a number of colorful figures from the history of America. Chief among those is Hemingway himself, whom Evan looks to as a literary role model with the same fervor that Dante looked to Virgil. Like Dante before him, Brady treats most of the inhabitants of hell with dignity and compassion, while never letting us lose sight of the fact that they died as unrepentant sinners in rebellion against God. Hemingway died a suicide, and with the suicides he dwells, but his story is far more complex—and sad.

Hemingway, as Brady presents him, rejects the pharisaical piety and tyrannical authority of his parents to pave his own way in a world whose evil and misery he considers incompatible with a loving God. Instead, Hemingway explains, he chose to find his own happiness by “going beyond the rules God laid down in the Bible so I could create all the meaning for my life I needed, as if I was writing another book. The best writing comes from the truest sentences, and the best living, the kind of living I aimed to live, came from willing the freest choices, from experiencing anything and everything that happens under the sun, whether or not God permits it” (87).

Like Evan, and Brady, Hemingway is deeply conscious of the evils committed by the human race: “abroad there was the Great War, then the Second World War and the fascists, then the Holocaust and the atom bomb, and at home in America, there was two hundred years of slavery, then segregation, Indian removal, and the reality we threw the slaves and the natives into the machinery of empire and ground them up until we enjoyed the highest standard of living the capitalist world ever saw” (88). Unlike Evan and Brady, who eventually find the remedy for this evil in the cross of Christ, Hemingway’s aborted struggle with evil led him to “abandon hope, hope in God, hope that choices really matter, hope that anything matters” (88).

In shaping his intellectual-emotional-spiritual portrait of Hemingway, as well as the other souls Evan meets in hell, Brady consulted a goodly number of primary and secondary sources that he references in his copious notes and works cited page. Though fictional and strongly imaginative, Brady’s Inferno is grounded in solid research. As such, it bears comparison with Plutarch’s Lives, providing moral biographies of the great Americans as Plutarch does for the noble Greeks and Romans. I shall close this review by considering briefly four of Brady’s most incisive portraits.


In Dante’s Inferno, a ferocious figure named Phlegyas ferries Dante and Virgil across the river Styx, avoiding the shades of the wrathful and sullen that dwell therein. In Brady’s Inferno, the ferryman is none other than Mark Twain. Like Hemingway, Twain is an author troubled by the evils of slavery, segregation, and lynching, and of the religious arguments used to justify such horrors. Like many people who reject God, Twain found the problem of pain—how it is that an all-good and all-powerful God could allow evil and suffering in the world he created—insolvable and so chose atheism.

If God didn’t care about evil, Twain explains, “why should he care how I live my life? What’s it to him if I live my life unto myself and enjoy a cigar every now and then? The conundrum was enough to drive a man like me to hell which, in part, it did—though o’course, maybe, I found the perfect excuse not to give my life to him…. For I made the same choice I gave to Huck: I’d rather go to Hell than float along the current of a corrupt and callous culture…. It’s hard not to reject God and everything he made or does in favor of the freedom that comes from being your own damned self, and I didn’t see much point then in giving up my freedoms for so little in return as a hard seat in church, a set of rules, and one long book” (43-44).

It will probably come as no surprise that Brady puts the suicidal lead guitarist and songwriter for Nirvana, Kurt Cobain, in hell; what is surprising, and refreshing, is that, in his portrait of Cobain, he goes beyond making the same old tired attacks on the evils of Rock & Roll. The core problem is not the music per se, but the disordered desire that motivates it. Like Hemingway and Twain, Cobain offers good reasons for his bad choices that Brady respects, and even pities, but which do not take away from his sin or his responsibility for that sin.

Here is Cobain’s “testimony”: “I was given a slow, ugly life, growing up in an awful town filled with drunk lumberjacks and unfit parents, where it rained every day and if it didn’t rain I got picked on at school. The only way I could escape a life of sad, white trash conformity was making music that said ‘f— you, universe,’ music that let everyone know life outside the womb was a barren, empty wasteland” (73). At first, Cobain did not seek fame, but when the dream of success hit him, he explains, “I gave every moment of my life to the dream and sacrificed everything to make it happen, only to figure out dreams aren’t real and to see everything I wanted in life—fame, success, genius, money, maybe a family—passing by me like a shadow marking time on a sundial” (73-74).

In the end, Cobain saw suicide as his only option out of a world that offered him nothing but pain and empty dreams. He points to his hope that his daughter would escape his negative influence as a factor in his suicide, and Brady allows for that possibility, but it does not take away from the sadness, despair, and disobedience of the act. In sharp contrast to punk rocker and grunge idol Cobain, Founding Father Benjamin Franklin seems a most unlikely candidate for hell; and yet, he too rejected both the authority and grace of God.

Franklin dwells with the heretics for he was a Deist who denied the divinity and atonement of Christ and who thought his good works would square him with the Creator. Rather than embrace the cross, Franklin explains, “I ventured upon a quest for moral perfection. In this, I took upon myself a new virtue each day: temperance, sincerity, justice, and the like. I recorded my progress on one day to improve upon that virtue on the next, all while striving to cultivate good character and subdue my passions in a manner I thought pleasing to the Maker” (96).

He heard the gospel preached by George Whitefield, but he did not see himself as a sinner in need of grace. Indeed, he confesses, as “I grew older, it became harder to see what need, if any, I had for Jesus, not when I convinced myself I was living each day just like Jesus would, imitating Jesus as a teacher of morals and a model of humility. Such is all I thought he was, and so I would neither live my life for him, nor give my life to him as my Savior” (98).

Another Founding Father Evan meets who was also guilty of domesticating Jesus into nothing more than a moral teacher is Thomas Jefferson. Punished as a false counselor for leading people astray by his edited Bible—a version of the gospels with all the miracles, including the resurrection, removed—Jefferson shares with Evan a heartbreaking story of how he came to reject the active, loving God of the scriptures.

After giving so much of himself to the founding of the American republic, Jefferson suffered a series of tragedies that took from him, in quick succession, three young children and his own dear wife. Amid this avalanche of death, Jefferson could not but feel abandoned by God. Having already helped to free his country from the despotic rule of George III, Jefferson “resolved to free mankind from yet another idle king. God had not helped me, not when such help might violate the laws of nature, laws God upholds against the prayers of helpless men, a truth now so wretchedly self-evident to me whenever I looked upon the graves of my children and my wife. I reasoned, quite easily, if Deism was true, then neither God nor Jesus performed the miracles recorded in scripture. Those miracles had to go” (161). And so he wrote his infamous Bible, cutting the divine Jesus out of the gospels as he had out of his own heart.

Brady introduces us to many other American icons, from a greedy Steve Jobs to a backroom-dealing Martin Van Buren, from George Troup, who initiated the Trail of Tears, to President Buchanan, who flattered slaveholders, from the treacherous Benedict Arnold to the envious, Lyndon Johnson. But I trust those I have discussed will make clear the power of Brady’s Inferno to dig down to the dark soul of mankind in general and America in particular. Those concerned for the future of our country, and their souls, ignore such a journey at their peril.

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The featured image is courtesy of Pixabay.

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