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In the aftermath of the 2016 election, calls to transform the Democratic Party through a mix of outside pressure and internal insurgency from grassroots progressives have further mounted in the age of Trump. Grassroots progressive political organizations present unique opportunities and constraints for political and social action. The resurgent relevance of grassroots progressive politics begs important sociological questions, particularly in the context of racialized political inequality, that remain unanswered. The increasing salience of the term “grassroots progressives” suggests an emergently influential collective political identity predicated upon identification with leftist politics and commitment to bottom-up democracy. Current debates and investigations of “political identity” routinely center on how partisan self-identification correlates with attitudes, beliefs, or support for policies and political actors. However, this approach often fails to capture the richness of political life as something profoundly active, dynamic, and social. I thus argue for analyzing the accomplishment of political identity and how it is influenced by both the choices people make and the social context that they inhabit. Understanding why and how people do things in their democratic participation is especially relevant within the social context of political and racial inequalities. Through an ethnographic case study, conducted during and after the 2016 presidential election, of a progressive political organization that I call the Grassroots Action Party , I demonstrate how political actors develop and express a political sense of self in their daily lives. I emphasize how participants produced and enacted grassroots progressive identity in relation to: (1) geographic and social contexts; (2) major political and social events; and (3) racial identities and meanings. By exploring the contours of grassroots progressive identity, this study uncovers processes that simultaneously (re)construct political identity and maintain and transform inequality and exclusion within the dual contexts of grassroots democracy and a racialized social system.