This chapter describes how Grace Lee Boggs engaged with radical politics upon her arrival in Chicago. After joining the Workers Party, she became a Trotskyist. She used her connections to the radical left to work with Chicago’s black community, wrote articles in the Trotskyite press in support of the March on Washington Movement, and eventually met C.L.R. James and joined the Johnson-Forest Tendency in splitting from the Socialist Workers Party. She ultimately helps form and publish Correspondence.