I should say right now that when we started this contest to determine the Greatest Ever Chicago Book, we knew it would be impossible to find one title that would satisfy every Chicagoan in terms of both greatness and Chicago-ness. Books don’t work that way. Neither does the experience of a city. Both of these things are entirely subjective, even more than the basketball tournament that inspired the shape of this contest. At least in basketball you can say that, in a particular game, one team sunk more baskets than another. We have no real objective standard like that for books, just our prejudices and our preferences, and maybe sometimes just a fleeting opinion or annoyance because we’re reading a cheap edition with tiny print and a binding that’s falling apart.

But we decided to go ahead and do it anyway, because we love books and we love Chicago and we love talking and writing and arguing about them.

If we were really imitating the NCAA, we would have started with 64 books. With all the reading involved, the tournament would have dragged on for a year, and everyone would have gotten sick of it, ourselves included. So we decided to go with the Sweet 16. We wanted to make room for not just realistic fiction and journalism but also fantasy and kids books and YA, and we wanted fair and logical pairings, so that a book about urban poverty wouldn’t be facing off against a novel about a middle-class marriage. This required—we might as well be honest—some arbitrary decisions, and naturally, almost as soon as we posted the bracket online, there were complaints. Why no Sister Carrie or Studs Lonigan or Sara Paretsky or The F***ing Epic Twitter Quest of @MayorEmanuel? Why Working and not Division Street, and why Chicago: City on the Make instead of The Man With the Golden Arm? And why reject all of this quality literature for two goddamned books by Mike Royko?

We were hoping someone would organize a competing book tourney—the National Invitation Tournament to our NCAA tournament—but so far no one has. Or at least we haven’t heard about it.

The next problem: How do you determine the winner in a book battle? By appointing a judge, of course, someone who is, in theory, impartial. (Though good readers never are.) We recruited 14 writers from around the city, including a few members of the Reader staff, asking them to choose a bracket, then read their two books and write an essay about which one they found superior. The winners would advance to the next round.

We offered no rules or guidelines for the judges. One of the most fascinating parts of the tournament was reading each judge’s reasons for determining which book was “better.”

Some judges decided Chicago-ness trumped literary greatness. “I believe this is a contest to discover the work of literature that best captures Chicago’s essence,” Jake Austen wrote in what was probably the most influential judgment in the tournament (at least in terms of how often it was discussed by other judges), the first-round bout in which he chose Working over Chris Ware’s Building Stories, although he considered the latter the superior work. “Thus, the nod of the construction helmet has to go to a book that deeply explores perhaps the most important Chicago archetype: the man doing an honest day’s work in a corrupt town.”

Others, like Bill Savage, based their choices on literary merit alone. “The real reason that Devil in the White City loses to Chicago: City on the Make is more about poetry,” Savage wrote in round one. “Larson’s book does not have a single memorable, much less quotable, line.” Two rounds later, though, Tal Rosenberg dismissed City on the Make in favor of The Warmth of Other Suns because of what he considered its overreliance on poetry: “Shouldn’t we as citizens and as readers reckon with the injustices of this city rather than overshadow them with mythology and folklore that exaggerates the past?”

Some were genuinely moved by the books they chose, like Marvin Tate, who wrote that The Time Traveler’s Wife‘s “continuous play with time conjured up anxieties in me that I thought did not exist or had, at this point in my life, been resolved,” or Peggy Shinner, who, though initially stymied by Working‘s lack of a conventional narrative, gradually fell under its spell: “The litany of loss, yearning, bitterness, pride; large and small fulfillments: together they acquired considerable heft.”

Some judges chose books for the messages they carried. “Bigger Thomas’s violent, criminal, and self-loathing character does more to foster the aggressive racial stereotype of black males than it does to offer a symbol of black rage,” Lance Williams explained when he rejected Native Son in round one. In round two, Mara Shalhoup favored The Warmth of Other Suns over The Jungle for its “small but genuine sense of hope.” Andrea Battleground chose The House on Mango Street for the same reason. “Chicago,” she wrote, “prepares people to become anyone they want to be.”

Opinions diverged sharply from round to round. “The stories in Mango Street are small for a reason,” wrote Wendy McClure in round two. “They’re small so that we can understand how perilously close they come to never being told at all.” But Brianna Wellen sent it packing in round three in favor of Working for a similar reason: “Fair representation of the city requires the voices and perspectives of many, not one.”

A few of the judges acknowledged the patent absurdity of a book tournament, particularly Danette Chavez, who had the most absurd bracket of all: I May Be Wrong but I Doubt It by Mike Royko versus Boss by . . . Mike Royko. “I can’t think of anything more ‘Chicago’ than a city that gave Daley the Elder his mayoral terms like so many punches on a ‘buy ten, get a free sandwich’ card,” she wrote in defense of Boss. “Unless it’s cops on the take, or cops gone wild on detainees, or appointments in place of elections. (Or how about pitting two Mike Royko books against each other in a tournament to determine the Greatest Chicago Book?)”

“Royko versus Algren. This is a tough bracket,” mourned Jerome Ludwig over his choices, Boss or Chicago: City on the Make. “I can hardly stand to choose one over the other.” He eventually resorted to an alternate method: comparing love letters by Royko to his first wife, Carol, to those by Simone de Beauvoir to Nelson Algren. “On the strength of that,” he finally decided, “Chicago: City on the Make advances. Just by a nose. (Not even by the length of Royko’s prominent beak. A much shorter nose than that: the nose of a Frenchwoman.)”

Of course it wouldn’t be a proper tournament without an upset. The biggest one probably came in round one, to the outrage of a few online commenters: “I Sailed With Magellan pulses with life,” Julia Thiel wrote. “The Adventures of Augie March is slow, soothing, almost hypnotic. Every time I picked it up, it immediately lulled me to sleep.”

Now that the dust has cleared, we’re left with The Warmth of Other Suns and Working. In some ways, it’s the most perfect and equal and, therefore, the toughest matchup of all. Both are massive, comprehensive examinations of a single subject—the Great Migration and work, respectively—that touches the lives of everyone in the city. Both rely heavily on oral histories. Both, ironically enough, have long stretches that take place outside Chicago. One has a long-standing place of honor in the Chicago canon. The other came out just five years ago. And both are great.

We’ve invited our judges back for one final ruling. —Aimee Levitt

Judge: Jake Austen

☐ The Warmth of Other Suns

☑ Working

Though colleagues have been kind praising my round-one championing of Working, I wouldn’t have chosen it as the Greatest Ever Chicago Book. Of the two tomes I was assigned, I argued that Working‘s artistic inferiority to Chris Ware’s Building Stories was trumped by Terkel’s supreme Chicago-ness. Yet I believed a book existed that, considering Working‘s flaws (not completely about Chicago, unspectacular prose), easily bested it. Unfortunately, I couldn’t name that book. I’d assumed Chicago had produced an unmitigated masterpiece, but perhaps that’s not our way. We don’t expect perfection, and can dig Algren despite purpleness, Wright despite pandering, and Royko despite hackishness. These shortcomings open the door for a Terkel tourney trophy, but my expectations weren’t Studs plowing through competition (like the Kentucky Wildcats) but, rather, meeting his unexpected match (like the Kentucky Wildcats). A fresher, more literary competitor could surprise the crusty coot, and I predicted a House on Mango Street bracket busting, as Cisneros’s writing is superior.

That’s also the case with The Warmth of Others Suns: Wilkerson’s novelistic approach to presenting hundreds of interviews has more depth, poetry, and variety than Studs’s capsules. Her Chicago passages shine brightest, and had they been the whole of Warmth, this would be no contest. But the best argument against Working is its non-Chicago content, and Warmth takes lengthy journeys to the coasts. Wilkerson earned her Pulitzer as a Chicago-based journalist, and Warmth‘s Ida Mae Brandon Gladney may be the most compelling Chicago character in literature. But the author wasn’t from here, didn’t stay here, and would neither consider herself a Chicago writer nor label her masterpiece a Chicago book. While I apologize for redundancy, like the heroes of Working I’m resigned to repeat the same labor, day after day. I once again choose a lesser work because anything its author touches drips Chicago like a dipped Italian beef.

Judge: Aimee Levitt

☑ The Warmth of Other Suns

☐ Working

I am sad to report that there’s a musical version of Working. It’s a terrible, terrible piece of theater, but unfortunately, my high school put it on the year I decided to be on stage crew, so all the songs are now lodged in my brain, and when I die I’ll probably spend eternity listening to it on continuous loop. I cannot read certain passages of Working the book without observing how they were bastardized and trivialized by the makers of the musical. And still, for years I’ve loved Studs, and more than any of his other books, I’ve loved Working. It’s virtually an encyclopedia of how people live and how they think about living. I taught it in a freshman composition class. I took it with me to journalism school as a reminder that the best way to learn about the world was by listening.

Sometimes, though, you need to do more than listen. Last fall, I finally read The Warmth of Other Suns for the first time. It was after Ferguson. The world was no longer as I had always understood it to be. Isabel Wilkerson listened to hundreds of people’s stories, and then she put them into context with the tools of a historian: laws, statistics, newspaper accounts. It knocked me out. And then, when I read Working again, it knocked that out, too, at least out of this tournament, as far as I was concerned. It’s not enough to look at how the world is and what people think about it, I realized. You have to understand how it got that way.

Judge: Jerome Ludwig

☐ The Warmth of Other Suns

☑ Working

On the day that I returned my borrowed copy of The Warmth of Other Suns to Sulzer Regional Library, I went up to the second floor to have a look around. On a long shelf there is a row of bound copies of the Saturday Evening Post. I have fond memories of being a youngster and reading the Post at my grandparents’ home in Kansas. Out of curiosity, I looked at some copies published around the time I was born, just to get a sense of the zeitgeist.

On the cover of the April 4, 1959, issue, the title of an inside story is noted: “Neighborhood Crisis: When a Negro Moves Next Door.”

This was all the more poignant after reading The Warmth of Other Suns. That being said, if I were all-powerful commissioner of the tourney, I would disqualify every book in the way of Native Son and award Richard Wright’s novel the title.

Wright himself was part of the Great Migration that is the subject of Isabel Wilkerson’s Final Two book. She writes of Wright: “He gave voice to the fears and yearnings of his fellow migrants through his novel Native Son and his autobiography, Black Boy. . . . He defected to the receiving station of Chicago, via Memphis, in December 1927, to feel, as he put it, ‘the warmth of other suns.’ ”

But I am not the commissioner, and Native Son lost out to The Warmth of Other Suns in round one. Still, I feel that for the purposes of a tourney such as this, the city itself should be a central character. It isn’t quite that in Warmth.

It isn’t quite that in Working either, but Studs was of Chicago.

Neck and neck all the way, a nail-biter, but Working wins on a last-second shot in overtime. And the crowd goes wild!

Judge: Wendy McClure

☑ The Warmth of Other Suns

☐ Working

I wish we had the option to declare a tie between Working and The Warmth of Other Suns. Being monumental, near-classic works, both about great untold American stories, they feel equally matched. But I think they also stand well together to show the course the tournament took and the judges’ collective notion of what the Greatest Chicago Book should be. We eschewed lone protagonists, nostalgic streetscapes, and Nobel laureates (much to the chagrin of a few of the online commenters); we weren’t guided by the need for certain kinds of canonical recognition, by visions of beloved icons, or proverbial women with broken noses.

We’re left instead with two excellent works of nonfiction, which seems fitting for a town that gave us The Jungle and There Are No Children Here as well Mike Royko and Roger Ebert and Eula Biss. And while neither of these books is about Chicago exclusively, they both are about pluralities and shared experiences, as were the other two books in the final four, Chicago: City on the Make and The House on Mango Street. I suppose the fact that we left those books behind in the penultimate round means that we favor the big stories over the more Chicago-focused ones—or it could just mean that we have common sense.

My own common sense tells me that if I must pick one book, it will be the one with the story that most urgently needed to be told: The Warmth of Other Suns.

Judge: Tal Rosenberg

☐ The Warmth of Other Suns

☑ Working

I’m partially responsible for The Warmth of Other Suns making it to the tournament final. In my round-three essay I wrote, “Should the greatest Chicago book not be by or about Chicago, but by an outsider who addresses Chicago’s problems in oblique and indirect ways, in empirical narratives that are indisputable?” Later, I remarked that I wasn’t sure I had the answer, but that I wanted to have other writers decide with me.

Studs Terkel was a larger-than-life character, but he wasn’t a Chicago outsider—being around him was like, as Jake Austen so eloquently put it, “freebasing Chicago-ism.” And I’m not sure Working is a better book than The Warmth of Other Suns. But in its sweeping portrait of people’s pursuits, and in its intimacy and realism, it feels like a better Chicago book. The Warmth of Other Suns is a big-picture story, but its portrait of Chicago and even America isn’t as comprehensive as Working‘s. And if there’s anything that defines Chicago, it’s people from places all over the world who come to this city to work hard doing the things they may or may not love doing, all for an indescribable purpose beyond mere survival, striving toward something ineffably noble.

Judge: Bill Savage

☑ The Warmth of Other Suns

☑ Working

Pondering the Reader‘s Greatest Ever Chicago Book Tournament, I recall a line I use when teaching Chicago literature:

All representations of cities are partial in two ways: they are incomplete, and they are biased.

That is, there is no way to represent the entirety of the city. (See Borges’s “On Exactitude in Science”; and Joyce’s claim that you could rebuild a ruined Dublin brick by brick from his fiction is Irish bull of the first order.) And any incomplete representation will necessarily have a particular point of view, an angle, that necessarily excludes some things. Look at the Loop skyline and you miss the steeples and smokestacks of the neighborhood skylines.

My own bias has always been towards the more complete Chicago books, books that represent as wide a range of people, places, institutions, and history as possible. That’s one reason why I picked Chicago: City on the Make over The Devil in the White City in round one, and why I politicked for Algren’s prose poem over Mike Royko’s Boss in round two. Algren’s text, by ranging further into history and across more of the landscape, encompassing more of Chicago, was simply less incomplete, less biased.

That said, I have to admit that the final round here leaves me baffled. Terkel’s Working is definitely more complete, representing a wider range of Chicagoans and their experience. But Warmth of Other Suns represents the central reality of Chicago, its history of aspiration and conflict and race, in such depth and with such mastery that it’s hard to choose.

So I won’t. Can we call it a tie?

Judge: Peggy Shinner

☑ The Warmth of Other Suns

☐ Working

I venture to say that most of us, Americans at least, see our lives as ahistorical. History happens in the past or to other people or, recently, in Indiana. It’s the exceptional, not the quotidian. We live our lives outside of it. Until we don’t.

Isabel Wilkerson’s The Warmth of Other Suns lands us squarely in the stream of history. That is one of its great triumphs and great rewards. I am a native Chicagoan. I love my city, in all its vexing complexity. But how little I have understood it or my place in it. I’ve taken its racial divides as an unfortunate and unscrutinized given, rather than a consequence of a systematic and cannily crafted set of policies. I have been, as Wilkerson suggests, “sublimely ignorant.” Or as journalist Ta-Nehisi Coates wrote: “The burden of whiteness is this: You can live in the world of myth and be taken seriously.” Ignorance is its own kind of myth, fastidiously recast by Wilkerson’s monumental story of the Great Migration. Chicago was one of its main destinations.

What is this historical moment? It depends who’s looking, of course, and from where. Ferguson, Eric Garner, Tamir Rice; the rise of “stop and frisk” in Chicago, which disproportionately targets people of color; we don’t serve gays, a sign that surfaced in Indiana, reminiscent of the ubiquitous colored only signs of the Jim Crow south. Jacob Lawrence’s epic Migration Series, now on exhibit at MOMA in New York. Coates, deeply influenced by Wilkerson’s book, making the case for reparations.

This, then, is the moment.

Judge: Julia Thiel

☑ The Warmth of Other Suns

☐ Working

Pinpointing the greatest Chicago book is a little like trying to shoot a shape-shifter: just when you’ve finally got it in your sights, it morphs into another form and slips away. (Or at least that’s what I’ve learned from TV.) Depending on your definition of “greatest ever Chicago book,” the title could go to almost any of the contenders. Does the emphasis go on “greatest” or on “Chicago”? Or on “book”? (Just kidding; they’re all books, though Divergent‘s haters might disagree.)

Having had quite a while to consider these questions, I’ve found I favor the books that are essentially love letters to Chicago: Chicago: City on the Make, I Sailed With Magellan, The Adventures of Augie March. (It’s true that in my round of judging I chose Magellan over Augie, which I mostly enjoyed as a sleep aid, but I still begrudgingly recognize the latter as a great book.) To me, they embody the greatest Chicago books.

But that’s not the question at hand.

As other judges have noted, it’s hard to find a Chicagoan who defines Chicago better than Studs Terkel, and Working is a lasting testament to his skill as an oral historian. Isabel Wilkerson, however, far surpasses him, seamlessly weaving the stories of three participants in the Great Migration together with the history of the mass exodus from the south. The Warmth of Other Suns is a book about 20th-century America, not Chicago specifically, but the portion dedicated to Ida Mae Gladney alone is enough to elevate it above Working, which isn’t dedicated entirely to Chicagoans either.

Judge: Brianna Wellen

☐ The Warmth of Other Suns

☑ Working

I’ll admit I had an agenda going into the Greatest Ever Chicago Book tournament. I was hoping to be the judge who would advocate against the dead white men who have epitomized this city for too long. It seemed like a perfect opportunity to officially acknowledge the diversity that makes Chicago the wonderful place it is.

But given the choice between two lovely works in round three, Working by Studs Terkel and The House on Mango Street by Sandra Cisneros, I was compelled to change course.

I chose the book by the dead white guy—and I’m doing it again.

While both Working and The Warmth of Other Suns are expertly constructed and provide distinctive views of the city, it is once again Terkel’s mastery of telling other people’s stories that seems to most powerfully represent the life and variety of Chicago.

It’s important to remember that a different set of 16 books could be read by a different group of judges, and the winner of that bracket could be just as deserving of the title. The Greatest Ever Chicago Book, as we’ve learned through these essays, means different things to different people. Who knows what books will come out of Chicago in the next ten years; within that sampling could be a masterpiece that captures the voice of city more accurately than we would’ve dreamed. I hope that happens, and I hope it’s a young nonwhite woman who steps up to the challenge.