• Sue Kwong

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.

Boss is a meaty book. Meaty like a juicy, big-as-your-head steak. There’s a lot to chew on here, all seasoned with peppery Roykoisms.

On the division of neighborhoods by ethnicity: “But you could always tell, even with your eyes closed, which state you were in by the odors of the food stores and the open kitchen windows, the sound of the foreign or familiar language, and by whether a stranger hit you in the head with a rock.”

But this follows soon after: “It isn’t hard to love a town for its greater and its lesser towers, its pleasant parks or its flashing ballet. Or for its broad and bending boulevards, where the continuous headlights follow, one dark driver after the next, one swift car after another, all night, all night and all night. But you never truly love it till you can love its alleys too.”

So, how to break the tie.

One is Royko in Love: Mike’s Letters to Carol. Michael Miner called it “one long promise from Mike Royko to Carol Duckman that he will love her the rest of his life.”

Dear friend

My precious, beloved Chicago man

Nelson, mon cher amour

Dearest darling you

Dearest naughty you

Sweetest faraway you

My own beast

My darling own beast

My own beastish beast

Sweetest you, sweetest of all monsters in the world

My nice faraway wrapped in the blizzard you

Dearest sitting and brooding local beast

My poor dearest American dilemma

Dearest Division Street Dostoyevsky

Dearest man with the golden arm

My man with the golden brain