Of Loopholes and Black Holes

(Alastair Bennett/Flickr Commons)

A Naked Singularity: A Novel
by Sergio De La Pava
University of Chicago Press, 2012, 688 pp.

In September 2008, the New York literary establishment took time from its anxious hand wringing over the uncertain financial future of the publishing industry to mourn the death of David Foster Wallace. Reminiscences by friends, colleagues, students, and famous former lovers occupied headlines and column inches; rumors of an unfinished novel generated page-views; and posthumous publications of everything from Wallace’s graduation speeches to his undergraduate philosophy thesis were planned. A writer largely regarded as the author of quirky, innovative essays with footnotes and a long, nearly-unreadable avant-garde novel with footnotes was officially recognized as the voice of his generation and transformed overnight into a kind of secular saint. But implicit in the literary establishment’s posthumous canonization of Infinite Jest as a masterpiece of American fiction was a cynical prediction: This will never happen again.

A month later, an unknown New York City public defender named Sergio De La Pava self-published his debut novel, A Naked Singularity, with Xlibris, an on-demand publishing service. The ambitious, dense, nearly seven-hundred-page manuscript had taken him six years to complete and had earned him rejection letters from nearly ninety agents, but De La Pava was not content to consign it to the drawer. With his wife acting as his publicist, A Naked Singularity found its way into the hands of Scott Bryan Wilson, a courageous reviewer at the online journal The Quarterly Conversation. Wilson looked beyond the Xlibris dust jacket and gave the novel an ecstatic review that launched it from total obscurity to near-total obscurity.

Other reviews followed, and the book was finally picked up last year by the University of Chicago Press, which rarely publishes fiction. From that distribution platform new readers are slowly discovering that A Naked Singularity is a masterpiece, not just “one of the best and most original novels of the decade,” as Wilson put it, but the sort of book that, if there’s any justice, would merit a place on any “best American novels of the twenty-first century” list.  (De La Pava’s second novel, also originally published by Xlibris, will be reissued by the press in October.)

Early critics of A Naked Singularity have accurately, if superficially, compared it to works by postmodernist heavyweights such as William Gaddis, Thomas Pynchon, Don DeLillo, and Wallace himself. True, the novel bears many of the hallmarks of postmodern fiction. Into his loose and baggy monster, De La Pava has stuffed a zany heist plot, mockuments and fictional transcripts, obscure references to philosophy and theoretical physics, his mother’s recipe for empanadas, a critique of Television capital T, a hallucinated Uncle Sam and his chimpanzee partner, and an inset biography of the career of the boxer Wilfred Benitez that parallels but does not intersect with the development of the novel’s protagonist.

But what most closely connects De La Pava to these stylistic precursors is that, like them, he has written a Systems Novel, which moves its characters through the machinery of the institutions that structure and regulate contemporary life as a means of critically investigating their effects on individuals. The particular System De La Pava has taken as his subject is not only the one that has a strong claim to being the most important and most pernicious in America today, but is also the one that suffers the greatest neglect from the upper echelons of our cultural and political establishments: the so-called Criminal Justice System.

The novel’s title, which refers to the infinitely dense core of a black hole, is borrowed from a hypothesis in general relativity. But perhaps it should be construed as a metaphor for the Criminal Justice System itself. Set during an unusually frigid winter in the early years of the twenty-first century, when the United States set the dubious record for incarcerating more of its citizens than any nation in history, A Naked Singularity is a descent into a world, our world, where crime and punishment have become increasingly indistinguishable.


Our guide into this moral black hole is a young New York City public defender named Casi. Born in New Jersey to Colombian immigrants as was his creator, Casi is a preternaturally talented litigator. Since earning his license at the age of twenty-two, he has never lost a trial. Of the novel’s many departures from strict realism, this last detail is perhaps the one that requires the greatest suspension of disbelief. As De La Pava shows, from arrest to verdict, the legal process inordinately favors prosecutors, rendering a perfect defense record practically impossible.

Casi’s abilities in argument are equaled only by his personal commitment to justice:

Until I quit, I thought, I could make a pledge like the kind comic book superheros are always making, you know where they like pledge that never again will injustice flourish in their presence and then this pledge brings a clarity and meaning to the superhero’s life that he or she could not have envisioned prior to the pledge. A Pledge. I decided to make one, a pledge, to myself really…in the mystical future, but the one that began like that instant, nothing detrimental or untoward would ever happen to a client of mine.

To keep his pledge, he works long hours on behalf of an overcrowded roster of clients, not including the pro-bono work he does on the case of Jalen Kingg, a mentally disabled black man who has been sentenced to death in Alabama. As a result, he barely has a romantic or social life. De La Pava introduces one romantic subplot, immediately squashes it, and then lets the thread of another dangle throughout the last act of the book. Outside the office, Casi’s only friends are his three wastoid neighbors, Alyona, Louis, and Angus. As “good customers of Columbia University,” they are “purchasing” useless degrees with their parents’ money, while they do little more than conduct conceptually sophisticated, but thoroughly inane debates about the latest developments in Television.

Unlike them, and unlike his former law school classmates, who have gone to work for corporate firms or private practices, Casi is barely able to pay his student loans or the high rent for a Brooklyn “apartment roughly the size of a manila envelope.” Debt collectors hound him; cabdrivers and distant relatives question his conscience. Voicing the average American’s view of Casi’s profession, they want to know how he can live with himself for “defending people [he knows] are guilty” and “representing the scum of the Earth.” In this respect, his situation is entirely typical. Today, there are material and social disincentives for those who would uphold the right to an attorney, which is supposed to be one of our most cherished legal protections. And yet, until the middle of the novel, when he is finally tempted into a life of crime, Casi’s sense of rectitude is so stringent that he refuses even to jump a subway turnstile “like countless former clients” to get out of the bitter cold.

The novel opens on the morning of his twenty-fourth birthday, the night Casi first crosses paths with Dane, at Central Booking, where the two are sharing arraignment duties. A fellow public defender, Dane is a recent transplant from Florida, but as a character, he can trace his ancestry to brilliant, talkative, larger-than-life monomaniacs like Captain Ahab, Recktall Brown, and Robert Coover’s Uncle Sam. Dane’s particular obsession is Perfection.

The idea was that I would pick a client at random…I would represent him in a manner that was not only flawless and resulted in the best possible result but my representation would also have the beautiful symmetrical quality found in all objects we deem perfect. In the end I’d be Time’s first human author of perfection.

Dane spends his every waking hour researching the life of Barnes, his chosen client. He researches the district attorney who would be prosecuting the case and every possible judge that might be called to try it. In order to perfectly prep Barnes for his cross-examination, he learns to think like him, which entails keeping a diary from his point of view, living in a house in his run-down neighborhood, surviving on his meager income, and even smoking crack like he does. He applies the same level of assiduousness to his jury selection and his summation. Dane’s efforts on behalf of Barnes are indeed superhuman, but one can’t help thinking that his concept of perfection would be the one that most nearly approximates the standard of representation to which every defendant ought to be entitled, the sort of representation that takes seriously the consequences of failure. The ideal Dane achieves would actually be possible, De La Pava suggests, if public defenders had better pay, smaller caseloads, and more adequate time to devote to each of their clients.

Or, I should say, almost achieves. During his summation, Dane takes a dramatic pause…and forgets how he is supposed to conclude. His client is acquitted in record time, but Dane is crushed by what he sees as defeat snatched from the jaws of victory. Yet, in his disillusionment, he does not give up on his quest for perfection. He decides instead to transfer the field of application—to the commission of a perfect crime. Using insider information from one of Casi’s former clients who has turned informant, Dane plans to double cross the police and an international drug kingpin and make off with millions of dollars in loot. For Dane, perfection stands above everyday considerations of justice and injustice, and also above pious homilies about an honest day’s work. He’s the sort of person that America produces every so often, the sort who would strike the sun if it insulted him.

In his pursuit of the perfect crime, he hopes to enlist Casi, in whose perfect trial record he sees evidence of a kindred spirit. Casi may be as virtuous as Dane is evil, but he has a classically American faith in the value of merit. If only he can be cleverer and harder working than his competition in the DA’s office, he reasons, he will be successful in upholding his Pledge. Casi’s intelligence is his strength and his weakness. His faith in the equation of truth and goodness is progressively chipped away by Dane’s arguments and finally broken when, in the face of an intransigent judge who sustains none of his objections and allows none of his arguments, he loses his first case. Although he vacillates for a hundred pages at a stretch—“you must decide whether you’re a Sinner or a Saint,” an exasperated Dane tells him—the two finally embark upon a heist made all the more risky and dangerous by Casi’s often absurd attempts to make their crime more moral (the two perform it with swords instead of guns). But even Casi’s solicitousness on behalf of the criminals he’s robbing does not prevent him from doing, in the end, serious damage to his principles and his sanity.


Whatever debt De La Pava owes to the formal techniques of postmodernism, he is also capable of delivering old-fashioned novelistic pleasures. We root for Casi and we worry about him—affective responses that are surprising in a book that is so unapologetically intelligent. The heist sequence is as much of a page-turner as any legal thriller. The correspondence between Casi and Jalen Kingg is genuinely heartbreaking, all the more so when one considers the latter’s close resemblance to actual death row inmates like Ricky Ray Rector and Warren Lee Hill. We feel indignation at treatment of Casi’s clients and the way the legal deck is stacked against them, an indignation that translates into indignation against the Criminal Justice System De La Pava is, unfortunately, only loosely fictionalizing. Indignation is possible because De La Pava never allows this system to recede into the vague cloud of paranoia or anxiety sometimes encountered in postmodern fiction; mass incarceration always remains, for Casi and his creator, a specific political problem rather than a general metaphysical condition.

Nor, finally, does De La Pava flinch from staging long, earnest conversations about questions of ultimate importance: Is there moral progress? Does God exist? Is there life after death? To what extent does the law create crime? Is it possible to eradicate racism? Again, such searching conversations remind one not so much of the heady theorizing of Pynchon or DeLillo, where ideas appear as gnomic sermons delivered ex cathedra by an authorial surrogate, but of the philosophical polyphony of a nineteenth-century novelist like Herman Melville or, indeed, Fyodor Dostoevsky. The difference, especially, is one of tone; unlike his contemporaries, De La Pava is unafraid to be serious rather than wry, passionate rather than self-consciously clever, morally and politically engaged rather than ironically detached. A Naked Singularity is that rarest of things: an uncompromising work of fiction that perfectly balances its aesthetic and its political commitments. It is the sort of book that Dostoevsky himself might have written had he come of age in early twenty-first-century New York rather than mid-nineteenth century St. Petersburg, training his sights on our country’s dual plagues of mass incarceration and irony, rather than on the serfdom and nihilism that plagued his own time and place.


Not that the publication of a single novel will have any appreciable effect on penal reform. It is almost impossible to imagine some future president, after a protracted struggle that finally ends mass incarceration and restores the legal protections eviscerated by the War on Drugs and the War on Terror, saying to De La Pava, “So you’re the little [defense lawyer] that started this big war,” as Abraham Lincoln is reported to have said to the author of Uncle Tom’s Cabin. (And that president would almost certainly not be Barack Obama, whose record on the issue is decidedly mixed.) This is not because the novel lacks moral force, but because the novel itself no longer captures the attention of the public the way it did in Harriet Beecher Stowe’s day. The political novel—not the novel whose subject is political, but the one that attempts to have political impact—is dead.

No one knows this better than De La Pava. Even though against all odds he’s finally had a taste of literary success, it hasn’t prompted him to quit his day job. When he told an interviewer that “at some point I decided I would devote my professional life to making a small dent” in the problem of mass incarceration, he was referring to his work as a lawyer, not as a writer.

The political novel—not the novel whose subject is political, but the one that attempts to have political impact—is dead.

Although the scholarly literature on mass incarceration is proliferating, novels like De La Pava’s are cries in the wilderness of declining reading rates, shuttered bookstores, and a moribund, risk-averse corporate publishing industry. One might ask whether the task of vividly depicting the human toll of America’s racist and excessively punitive legal system would be better left to a medium such as television, which actually reaches millions of Americans.

Unfortunately, television, at least in its current state, is part of the problem. Television encourages the very ironic detachment that makes genuine engagement with our degraded moral landscape more difficult and, indeed, can make us more cynical about cruelty and indifferent to injustice. This is what De La Pava portrays in the Television subplot that takes place at Casi’s neighbors’ apartment. Although on first read this section seems to be the weakest, a rehashed DeLilloan media critique, on a second read its presence becomes more clearly a necessary part of De La Pava’s overall moral vision.

Halfway through the novel, Casi joins Alyona, Louis, and Angus as they watch ADTV, the purest channel on Television, one that only shows advertisements, without interruption, twenty-four hours a day. Besides the ads, the only sound that can be heard is the zapping that comes from the electrified floor of a large transparent cage in which Louis has trapped a large black rat for the purposes of a psychological experiment.

Casi begs, argues, and pleads with his neighbors to release the rat, but the three are too busy watching Television to give much thought to the rat’s suffering; they even attempt to come up with reasons why the rat deserves to be tortured.

In a single image, the parallel is made clear: Casi’s neighbors are us, and the rat our penal population. While they are confined and tortured in plain sight, we spend our time in thrall to debased entertainments, including those that depict, nearly always from the point of view of the legal system itself, heroic prosecutors capturing and punishing racialized caricatures of criminals. We use the same ironic detachment to rationalize their suffering and our indifference. If Dane uses his intelligence to commit a spectacular injustice, Alyona, Louis, and Angus allow injustice to occur while they waste their intelligence on petty spectacle.

Thus, the importance of the medium cannot be discounted. And implicit in De La Pava’s novel is a vindication of the form. Although it is no longer the newest art, nor the easiest to digest, nor the most cost-efficient to deliver to a large audience, the novel is still the medium that allows time and space to serious considerations about how we organize our society and how we organize our lives. In the past thirty years our art has grown less serious and our politics more cruel. It has taken a novel of the artistic ambition and moral seriousness of A Naked Singularity to show us why this is no coincidence at all.


Ryan Ruby is a lecturer in philosophy at York College in Queens. His fiction and criticism have appeared in Conjunctions, Bookforum, the Baffler, n+1, and elsewhere.