In his time and since his death, Saul Alinsky (1909–1972) has cut a steady swath through American political culture. Given, though, that his name is invoked more frequently in partisan circles, his work and legacy is largely misunderstood. Alinsky was, and remains, a recognized provocateur against economic and political forces that upheld de jure and de facto discrimination: He took on powerful institutions like the University of Chicago, Mayor Daley’s Chicago machine politics system, the Eastman-Kodak corporation, and anybody else who stood in the way of a fuller realization of democratic principles. At his core, Alinsky was an educator who taught economically-disadvantaged Americans to confront systematic racism and classism and, most importantly, develop a set of public skills that allowed them to get what they deserved, namely, fair and decent housing, equitable pay, and basic city services. And, as I explain in this article, Alinsky did all this with a large dose of humor, irreverence, and ridicule toward authority figures.