In 1964, Haywood worked in Harlem with Jesse Gray, leader of the Harlem Rent Strike and Tenants' Union later elected to the New York State Legislature from Harlem. Haywood worked with Malcolm X in 1964 until his assassination in 1965, and with James Haughton and Josh Lawrence in Harlem Fight-Back, then in Oakland, California, in 1966, then in Detroit, Michigan, with the Detroit Revolutionary Union Movement (DRUM) and the League of Revolutionary Black Workers.
In 1964, Haywood interacted with Jesse Gray, leader of the Harlem Rent Strike and Tenants' Union who later became a New York State Legislature representative from Harlem. Haywood collaborated with Malcolm X until his death in 1965, and worked with James Haughton and Josh Lawrence in Harlem Fight-Back. In 1966, he was active in Oakland, California, and then in Detroit, Michigan, with the Detroit Revolutionary Union Movement (DRUM) and the League of Revolutionary Black Workers.