Across the United States, a counter-network of teacher activists is engaged in the development of grassroots organizing structures to advocate for social justice, resist the privatization of public education, and increase union democracy. The United Caucuses of Rank and File Educators (UCORE) is a national network of more than 20 union reform caucuses from both the National Education Association (NEA) and American Federation of Teachers (AFT). The subject of this chapter is Organize 2020, the UCORE member caucus from North Carolina. As the second least unionized state in the nation, North Carolina offers an unusual and revealing context in which to conduct a case study of grassroots organizing structures. The contribution of this study relates to the context-specific ideas, experiences, and activities of the caucus members interviewed. The political challenges faced by North Carolina teachers are not, however, entirely unique. The accounts of Organize 2020 members therefore provide some valuable insight into the types of strategies educational organizers can use in a state with weak labor laws.