If C. L. R. James could later reflect in Beyond a Boundary that before arriving in Britain, “about Britain, I was a strange compound of knowledge and ignorance,” then the same was fundamentally true about his relation to American society before his arrival there in 1938. This article will begin with discussion of the attraction of America for black West Indians, including George Padmore, in the era of the Harlem Renaissance, as well as the young James's own love of jazz and American literature. The complexities of the young James's “anti-Americanism” will be also explored, before we explore how James's turn to both Marxism and pan-Africanism after 1934 led to a new appreciation of both the power of the American working class and a new understanding of how a revolutionary solution might be found to the “Negro Question,” the question of the systematic racism towards black people in America. The article will conclude with discussion of James's 1938 work A History of Negro Revolt, in particular its Marxist analysis of the history of American slavery and its abolition during the American Civil War, as well as the strengths and limitations of Garveyism as a social movement.