Originally we intended to let the round one judges petition the round two judges on behalf of the books they thought should advance, but early on, that format fell by the wayside. For one thing, a few of the judges had to bow out for various reasons (though one sent along an impassioned argument by proxy) so there was no one there to represent every single book. And, for another, in a tournament like this, it's not so much which book is better as which one the judge thinks is better. The outcome depends entirely on arbitrary decisions. And some, as our judges have admitted, have been very hard to make.
And so the conversation evolved into what makes a great Chicago book. Is it the greatness of a book that happens to be set in Chicago or written by a Chicagoan, or is it something more ineffable, something in a book's DNA that makes it and the city inextricable, like the combination of Mike Royko and Richard J. Daley in Boss, or, more abstractly, the way the city's architecture and design history run through Building Stories? Is the idea of a Chicago book limited by the Chicago stereotype of the tough neighborhood guy, the worker laboring in the gritty, dirty city? How do the more recently published entries in the tournament, like The Warmth of Other Suns or The Book of My Lives expand the canon? Can't there be room for fantasy and romance, too, like Divergent and The Time Traveler's Wife?
It was a fun discussion. It didn't resolve anything, but it wasn't meant to. It was just meant to get everybody thinking. Afterward, my friend Mark and I wandered around Hyde Park and the university for an hour or so while we waited for his wife and daughter to finish up a play date and meet us for dinner, and we kept talking about great Chicago books and what makes a great Chicago book different from, say, a great New York book or a great Saint Louis book. (These are the only other cities we felt we could discuss with any authority.) Most of the great Saint Louis books end with the main character leaving, which seems to reflect the general life path of Saint Louis writers. In New York, and in New York books, you're always looking ahead for the next thing and scheming ways to move up in the world, and your greatness is measured by how far you move. In Chicago, you become great by sticking around, by knowing as much about the place as you can. Longevity is key. (As, perhaps, exemplified by the Mayors Daley. Or Studs Terkel. I saw him give a lecture once, when he was in his 90s, and he claimed that, while he'd be waiting for the bus outside his apartment in Uptown, complete strangers would walk by and say, "Hi, Studs!")
I thought about it some more as I drove home (up Lake Shore Drive, which is not gritty or proletariat, but still one of the most glorious Chicago things I can think of), and I realized that almost all the books in this tournament have this quality in common: the people who wrote them know—or knew—Chicago extremely well and described the city they knew. This goes beyond a mere sense of place; how hard is it to describe the lake anyway? (And yet, we get so pissed when writers who clearly know nothing about Chicago make an attempt at it and get it wrong.) Some, like Isabel Wilkerson and Upton Sinclair, learned it by research and reporting. Some, like Studs and Royko and Algren, learned it by talking to as many people as they could. Some, like Sandra Cisneros, Stuart Dybek, and Audrey Niffenegger learned it just by growing up and existing here. And others, like Aleksandar Hemon and Chris Ware and Jane Addams, arrived as adults and fell in love.
Of course there are other writers in other cities who understood their towns just as well. And of course people leave Chicago all the time. But our great books don't reflect that. (The one exception may be Sister Carrie, which we did consider for our sweet 16. But Carrie's ambitions take her away from Chicago to New York. That's more of an American story than a particularly Chicago story.) They're not about wanting to move on to the next big thing or lighting out for the territory. They're about being here for the long haul, about staying here for so long that they become not just part of Chicago, but Chicago itself.