Since the colonial era Cuba has been the paradigmatic case of a monocultural export economy, dependent upon the production of one primary commodity – sugar – for sale to one principal trade partner. Overcoming dependency was a high priority for Fidel Castro in 1959, yet despite a promising start, his efforts proved ultimately unsuccessful. Only the collapse of communism in Europe freed Cuba from dependent trade relations with the Soviet Union – albeit at the cost of enormous economic disruption. This article examines Cuba's post-1959 pursuit of economic independence, first to explain why the government's initial successes proved unsustainable in the 1980s, and then to examine Cuba's attempt to reinsert its economy into the global market in the aftermath of the Cold War.