This winter, the Reader has set a humble goal for itself: to determine the Greatest Chicago Book Ever Written. We chose 16 books that reflected the wide range of books that have come out of Chicago and the wide range of people who live here and assembled them into an NCAA-style bracket. Then we recruited a crack team of writers, editors, booksellers, and scholars as well as a few Reader staffers to judge each bout. The results of each contest will be published every Monday, along with an essay by each judge explaining his or her choice. The Reader reader who best predicts the judges’ rulings will win a trip to Mexico.

In this week’s contest, Reader Agenda editor Brianna Wellen has to choose the book that will go up against The Warmth of Other Suns in the tournament final: Working by Studs Terkel or The House on Mango Street by Sandra Cisneros. To see the results of previous bouts, look here.

On the surface, Working and The House on Mango Street couldn’t be more different. One is a 500-plus-page collection of interviews conducted by a middle-aged white man while the other is a barely-100-page reflection on growing up as a young Latina. But what they share is what defines a great Chicago book: a window into unique, everyday experiences on the streets of our fair city. While they’re both great in their own way, the time has come to decide which one is a contender to be Chicago’s greatest.

There’s no denying Studs Terkel’s influence on Chicago. As judge Jake Austen argued, “Terkel’s talents as a celebrator of Chicago’s everymen and everywomen is unmatched.” True. But when I first delved into the beastly work, one that I had never read before, I immediately became concerned that the strokes were too broad. Here we go again, I thought to myself. Another white dude thinks he has the final say on the human experience. However, once I got past the steel mill worker and the equipment operator and the nearly 40 pages of Terkel’s introduction before the book even really begins, it became clear why all 590 pages are necessary. Yes, there are the stories we’ve all heard before about factory workers in the city and white men overcoming obstacles to provide for their families. But there are also the stories of an airline stewardess, a black police officer, a washroom attendant, men and women of all ages and races from all across the city. Terkel proves his mastery in gathering the great many specific eccentricities that color the city streets.

While I had never so much as glanced at a copy of Working before this tournament, my experience with The House on Mango Street dates back to my freshman year of high school when it was required reading. The language spoke to me in a way that has kept me revisiting the work time and time again. As a pure exercise in writing, it’s a far more interesting read. Sandra Cisneros’s short, poetic vignettes are engaging in their simplicity while deftly capturing the complexities of a young woman’s journey to adulthood. Another tournament judge, Andrea Battleground, nailed it when she wrote, “Mango Street is a book to read to confirm that Chicago prepares people to become anyone they want to be.” Esperanza’s story is one that is rarely told as part of Chicago’s narrative, and in that sense, it’s a more compelling representation of the city. It’s a new view to many readers and addresses evolving issues of gentrification that have only become more relevant since the book’s publication.

So where does that leave us? It leaves us with an unfair battle, if you ask me. We have an oral history and a memoir-style novel, both exceptional works of literature and neither exclusively about Chicago—Mango Street is focused on a single character in a single neighborhood while Working travels to New York, LA, and rural parts of the country. Both are worthy of a second or third read and invite endless revisitation. I’d like to give them both the title, but, dammit, that’s just not how competitions work.

I felt a lot of pressure diving into this bracket. Who’s to say that I, a lowly millennial (as much as I hate to classify myself as such, my birth date traps me in that generation), should be the deciding voice on what best captures the literary voice of a city that’s more than seven times my own age? Well, that’s just it: a great book transcends age and gender and class and even personal experience.

As I struggled to choose between two books I have grown to love, the competition was so close in my mind that I had to leave our planet to make a decision. If I had to capture the Chicago experience in a capsule shot into to space so that an outsider completely uninitiated with humanity would understand, I would cryogenically seal up a Portillo’s hot dog, a parking ticket, and a copy of Working. Fair representation of the city requires the voices and perspectives of many, not one, and that is where Working outpaces Mango Street. You win again, Studs.

Working was the favorite among Reader readers as well. Voting for the final round in the tournament to determine the Greatest Chicago Book once and for all begins April 6.