The article aims at analyzing the constellation of domestic and international factors thai have led Ukrainian transformation efforts to standstill and produced long-term deteriorating outcomes for all spheres of society and major segments of population. The paper also questions the validity of background assumptions of "transitology " and attempts to evaluate their relevance to the analysis of post-Leninist Ukraine socio-political realities. Research strategy employed in the paper seeks to combine findings of the world system perspective and state-centered approach as well as to invoke classical social and political theory tradition for the analysis of the post-Leninist sociopolitical transformation.