The authors developed a fondness for Chicago sports and its heroes by the time they reached six years of age. They managed to forge lifelong friendships with many sport legends ranging from George Halas, founder of the National Football League and owner/coach of the Chicago Bears for whom the twins served as clubhouse boys during their high school years of 1963 through 1967; to Bobby Hull and Stan Mikita, Hockey Hall of Fame members of the Chicago Blackhawks; and to Yosh Kawano, legendary Chicago Cub clubhouse manager. They also forged a friendship with Frank Shorter, Gold and Silver medals winner in the 1972 and 1976 Olympic marathons. These friendships led to interactions with countless celebrities in the sports, entertainment, and political arenas. Combined with a caring and supportive family, the friendships set the authors out on an unexpected journey. The authors intersperse their stories with discussions of familial, educational, and vocational experiences. They provide a narrative of an era when neighbors seemed more connected to each other and Chicago's professional athletes seemed more connected to their fans.