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As a learning scientist and educator, I am deeply committed to developing meaningful civic and political learning experiences that take seriously the identities, lived experiences and dreams of young people, particularly those from marginalized communities. This commitment was shaped during my time as a special education and social studies teacher, including time teaching in Chicago Public Schools while Karen Lewis was Chicago Teachers Union (CTU) president. Lewis and the CTU’s Caucus of Rank-and-file Educators (CORE), transformed, broadened, and democratized educators’ relationship to the collective bargaining process. By asserting the CTU as an antiracist union and building multiracial coalitions with community organizations with long histories in Black and Brown neighborhoods, CORE created connections between our role as educators and broader social issues and social movements—including the Black Lives Matter Movement. Under Lewis’s leadership, the CTU also established a research department and produced reports, providing models for how unions can use research and organizing to shape policy. As a former district administrator and currently working in philanthropy, Lewis’s work and legacy provide important insights into how we might all learn together to build deep collaboration across practice, research, and policy to advance educational justice.