This chapter examines 16-inch, no-glove softball, described by one enthusiast as “Chicago's game,” and suggests that it is an “important part of the city's heritage.” Throughout the 1930s and1940s, softball provided Chicago with sports heroes and some of its most colorful sports moments before television. Following the 1933 World's Fair, softball became a professional sport in Chicago. Virtually unknown outside the city's greater metropolitan area, Chicago-style softball is played with a larger, softer ball called the “Clincher” fielded by ten position players (the tenth usually stationed behind second base) with their bare hands. At the beginning of the twenty-first century, 16-inch softball in the city proper remains strongest with African Americans. This chapter traces the history of 16-inch softball in Chicago and argues that the sport was not only an expression of traditional class and gender identities and relations, but also instilled a distinct sense of community among those who played and followed it.