• Sue Kwong

Last March, as it does every year, the Morning News held its annual Tournament of Books to determine the best book that was published in 2013. It coincided, as it also does every year, with the NCAA tournament to give those of us who have no interest at all in college basketball or loyalty to any team participating in the tournament (either because we did not attend Division I schools, or because our Division I school is notoriously sucky at men’s basketball) something to get excited about during the last depressing, slushy, muddy month of winter.

By the time August rolled around, February and March had become a distant, but still visceral, memory—especially when the first rumors emerged that we were facing another shitty winter. We at the Reader decided we needed to prepare, to plan ahead, even beyond stocking up on the finest whisky we could find on sale. It would be wrong to do our own 2014 Tournament of Books since the Morning News does it so beautifully. But what about a tournament of books that mattered to us—say, a tournament to determine the Greatest Chicago Book Ever Written that will also cheer up our frozen Reader readers and give one lucky soul a trip for two to Mexico?

We thought for a while, and came up with a pool of 16 titles that demonstrated the wide range of books that have come out of Chicago, fiction and non, from classics to journalism to graphic novels to history to young adult. We assembled them into a bracket.

  • Sue Kwong

But how to decide which book is better than another while still letting our readers play along?

To that purpose, we’ve recruited a crack team of judges whose judgment and writing we respect, a group of authors, editors, critics, booksellers, and scholars from the north, south, and west sides. They are:

Jake Austen, journalist, editor of Roctober, host of Chic-A-Go-Go, and coauthor of Darkest America: Black Minstrelsy from Slavery to Hip-Hop

Andrea Battleground, books editor of the AV Club

Jerome Ludwig, reviewer, bookseller, and former Reader managing editor

Wendy McClure, author of The Wilder Life: My Adventures in the Lost World of Little House on the Prairie, I’m Not the New Me, and the Wanderville series for kids; columnist for Bust; and editor at Albert Whitman and Company

Bill Savage, coeditor of Chicago by Day and Night: The Pleasure Seeker’s Guide to the Paris of America and the 50th anniversary critical edition of The Man With the Golden Arm, Northwestern professor, and bartender

Peggy Shinner, author of You Feel So Mortal: Essays on the Body and Northwestern professor

Marvin Tate, poet, author of School Yard of Broken Dreams and The Amazing Mr. Orange, and writer for the album, Tim Kinsella sings The Songs of Marvin Tate with Leroy Bach and Angel Olsen

Lance Williams, coauthor of The Almighty Black P Stone Nation: The Rise, Fall and Resurgence of an American Gang and professor at Northeastern Illinois University

We also recruited a few more judges from the ranks of the Reader staff: Mara Shalhoup, Danette Chavez, Tal Rosenberg, Julia Thiel, Brianna Wellen, and me.

Each judge has been assigned a bracket. (Check out the chart above to see who’s judging what.) He or she will read both books, decide which one deserves to advance, and prepare a summary of his or her judgment.

Now here’s where you come in. Can you predict how the judges will judge before they judge? Do you have special knowledge of their thought processes? Or is it just obvious to you which of these books is better than its opponent? Well, don’t just keep it to yourself. Vote here! Do it before midnight this Sunday, November 23. Remember, your honor and a trip to Mexico are at stake.

We’ll be keeping track of your predictions. If you predict everything right, you’ll be invited to submit your predictions for Round Two. The people who do the best job of predicting all the winners—that is, who predict all the winners correctly for all four rounds—will be entered to win a seven-night trip for two from Apple Vacations to the Riu Jalisco resort in Riviera Narayit, Mexico, just outside Puerto Vallarta. That’s right: after four months of reading about Chicago, you get to go to Mexico.

If you don’t win Round One, though, don’t despair. Try your luck with Round Two! At the end of each of the first two rounds, there will also be a drawing from the entries who correctly predicted the outcomes of each of the matches. The winner of each drawing will receive a $50 gift certificate from Barbara’s Bookstore.

Judges will reveal the winner of each bracket in essays that we will begin publishing next Monday, November 24 and run every Monday until January 12. Voting for Round Two begins immediately afterward, on January 13 and running through January 18. The judges begin issuing judgments the following day. Voting for Round Three begins February 10 and runs through March 1; the judges will begin handing down their decisions on March 2. And, finally, voting on the ultimate greatest book begins March 10 and runs through April 5. We’ll reveal both winners, the greatest book, and the name of the lucky reader who gets to go to Mexico, in our Spring Books Issue on April 16.

So make your predictions. Then stick around to cheer on your favorite book. It all begins next Monday.

The fine print:
Voting runs as follows:
Round One: November 19-November 23, 11:59 PM
Round Two: January 13-January 18, 11:59 PM
Round Three: February 10-March 1, 11:59 PM
Final: March 10-April 5, 11:59 PM

Apple Vacations is pleased to confirm one seven-night trip to Riu Jalisco, in Riviera Nayarit, Mexico for two adults departing from ORD, Chicago. Trip includes seven-night accommodations, round-trip charter air, transfers to/from resort, non-motorized watersports, all food/drinks at the resort and the assistance of an in-resort Apple Representative. Trip is valid for travel through August 1st, 2015. Taxes, insurance, any applicable baggage fees, and additional expenses (such as optional excursions, spa treatments, phone calls and souvenirs) are the sole responsibility of the winner. All vacations are subject to availability. Blackout dates do apply. This trip is valid through Aug. 1, 2015. Travel is not permitted during holiday periods including both 5 days prior to and after. Trips are non-transferable and cannot be exchanged for cash. Apple Vacations reserves the right to substitute the vacation with another of equal value, equal Apple rating or within the same hotel chain should any unforeseen circumstance occur. Hotel to be determined by Apple Vacations. Winner must be at least 21 years old or traveling with a legal guardian. Employees of participating companies and its properties, sponsors, vendors and their immediate families are not eligible to win. All departure/immigration taxes, insurance and fuel surcharges (approximately $310-380 USD per person, subject to change) must be paid by winner to Apple Vacations prior to departure. For full contest rules, click here.