The rise of Cuban sugar production from 1800 to world dominance in the 1920s is briefly portrayed, together with its collapse, recovery and subsequent stagnation between the 1930s and the Revolution of 1959. The renewed and further growth of the sugar economy from 1959–89 is considered in the context of the uniquely favourable terms of trade then developed with the USSR and COMECON. These provided expanding markets and financed the technical transformation of the cultivation, harvesting, transhipment and processing of the sugar cane. From 1993 to 2002, following the implosion of the USSR and the dissolution of COMECON, Cuba could produce little more than one half of the average annual sugar output of the 1980s. This collapse and the inability of the island's planners to reverse it are discussed with particularly emphasis on post-1997 efforts to stabilise production and lower costs to meet persistently unfavourable world market sugar prices. A critical appraisal of the drastic ‘restructuring’ programme announced in 2002 is illustrated by primary data collected in fieldwork in 1994, 1996 and 2002 and Cuba's dramatic post-1991 decline from dominance in the international sugar trade is stressed.