Community organizing emerged as a coherent mode of intervention under conditions of postwar Fordism, a set of economic and political conditions that have changed substantially. The three critiques of classic organizing models, built by Saul Alinsky and subsequently adapted by others, point to the need to cross formal, informal, and conceptual boundaries. To date, little is known about whether, and to what end, organizers take up the proposals of these critiques. This article responds to this empirical gap with an analysis of the critical case of community-labor organizing in Chicago. We find that Chicago organizers engage in the boundary-crossing practice that observers have long recommended, by focusing on basic organizing and the recruitment of the economically marginalized and racial minorities; developing new collaborations across racial, territorial, and issue boundaries; and shifting daily practices to engage in political education, thereby connecting neighborhood struggles to structural problems and broader political coalitions.