The economic performance of Belarus has been unimpressive ever since the fall of the Soviet Union, due mainly to the country’s lack of serious structural reforms. This study examines the consequences of this benign neglect should a democratic transition occur and attempts to understand the assistance that may be required to help Belarus successfully transform. Unlike the transformations which began in Central Europe during 1989, though, Belarus’ potential transition is complicated by immense Russian pressure. Hence, the provision of much needed assistance will be highly dependent upon Russia’s stance towards a democratic transfer of power. This study examines its possible responses to understand how the EU can best be involved in the long-delayed Belarusian transformation and also how much assistance may be required.