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.

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.

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.”

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.

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: Jerome Ludwig

☐ The Warmth of Other Suns

And the award for Greatest Ever Chicago Book goes to . . . 

After five months, 16 books, and four rounds, the final tally came to four votes for Working, six votes for Warmth (which included the ballots of judges Andrea Battleground and Danette Chavez), and one declaration of a tie. It must be noted 80 percent of the respondents in the final round of our readers’ poll predicted Warmth would best Working. Sorry, Studs.  v