This chapter traces Césaire’s rejection of departmentalization, his resignation from the French Communist Party, and his founding of the independent Parti progressiste martiniquais in 1958. It explores Césaire’s embrace of Senghor’s vision of cooperative federalism as a new legal status for Martinique, which he hoped to transform into an autonomous region of a new federal republic. The chapter argues that Césaire’s federalism was mediated by the legacy of Toussaint Louverture’s 1801 constitution for Saint-Domingue. Suggesting that Toussaint addressed a future that had not yet arrived, the chapter contends that Césaire’s public acts at this time were in dialogue with Toussaint as if the latter were a contemporary. It also discusses Césaire’s cautious support for de Gaulle’s French Community under the Fifth Republic and his progressive disillusionment with de Gaulle’s government. It explores his tense relationship with fellow Martinican communists and the labor disputes and general strikes in Martinique in the 1950s. It relates Césaire’s support for autonomy in his critical writings about decolonization, in his poetry, and in his landmark plays The Tragedy of King Christophe and A Season in the Congo.