In an attempt to better understand the complexity of American racism and democracy, this paper explores racism through the plight of an African American sharecropper, Odell Waller, and the reaction and involvement of John Dewey, America's most liberal democratic philosopher of the 20th century. This exploration delves into the nature of American justice in one of the most difficult struggles in our history, the late years of the Depression and the early years of World War II. Furthermore, the paper traces Dewey's limited discussion of race and his involvement in attacking racism in American society.