Why We Root: Mad Obsessions of a Chicago Sports Fan is a collection of Jack M Silverstein's sportswriting, including pieces from 1999 to 2023 that reveal the sports-fan mindset and show readers why we root for our teams. This collection of eighty-one articles is organized based on a fan's emotional journey—from learning the game, to knowing the game, to emotional heartbreak, and eventually to celebrating championships.

Included in the book are Silverstein's real-time articles on many of the best known Chicago sports events of the early 21st century, including: the White Sox, Blackhawks, and Cubs breaking winning their first championships after massive droughts; the Bears reaching, and losing, the Super Bowl; the rise and fall of saviors-to-be Derrick Rose and Jay Cutler; the Chicago Sky winning the 2021 WNBA championship; the Blackhawks' famed "17 seconds" championship; the Bears' agonizing "double doink"; and the Cubs' horrific Bartman game, retold from multiple perspectives in multiple years, including ten years later by pitcher Mark Prior and catcher Paul Bako. Also included are Silverstein's look back at the Bulls-Pistons rivalry of the 1990s, the 1995 Northwestern Wildcats Rose Bowl team, and Michael Jordan's flu game.

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