The Cubs-Cardinals game on June 23, 1984, served as a national coming-out party for Ryne Sandberg, the Cubs’ 2nd baseman who later earned National League MVP honors following that ’84 season. Twice, Sandberg faced future Hall of Fame closer Bruce Sutter as the tying run in the Cubs’ last at-bat. Twice, he homered to the bleachers in left field to extend the game, which was later won on a walk-off single by Dave Owen. Subsequently, the game became known by a simple yet infamous moniker: "The Sandberg Game."

PR Exec, Ted Gout, loses his big promotion to a fresh out of college know-it-all who has the upper hand when it comes to technology, driving Ted to embark on a low tech, old school journey to find himself - with his husband and friends in tow.

Using the frame of opening day, 2006, this documentary examines the Cubs' 100 years without a World Series title. Between conversations with a half-dozen selected Cubs fans in 2006, the film looks back at the Wrigley years, sale to the Tribune, and coming oh-so-close in 1945, 1969, 1984, and 2003.