This paper examines the implementation of agrarian reform by the Rebel Army and their first attempts at state formation in the liberated territories. Analyzing polemics around Communist contributions to the insurgency, this paper recasts initial attempts at land reform as a crucial element to Cuba’s eventual positioning within the Cold War, and places the 1958 insurgency into conversations about anti-colonial and anti-imperialist global revolutionary change. Using rare documentation from the Sierra Maestra, this paper argues that the ways in which pressures exerted on guerilla leaders by peasants, communists, and anti-communist revolutionaries during the war competed against each other set the revolution on a particular path, even before it had been won. Finally, this essay incorporates an often overlooked group of black radical peasants into the historiography of the Cuban Revolution, arguing that in their negotiation with guerrilla incursions they helped shape what would eventually become the Revolution’s social, economic and agrarian policies.