The present paper constitutes an attempt at examining, in a comparative fashion, the processes of decentralization in three countries of former Sovietized Europe, and the repercussions they entail at the local level. The decentralization of public services represents a perennial point on the agenda of the postcommunist governments in East-Central Europe, while its realization and implementation has yielded mixed, rather controversial results: on the one hand, observers and decision-makers praise the benefits of “local autonomy” and independent public policy at the local level, accompanied by a more meaningful citizens’ participation, on the other hand, contestations are voiced through the prism of what is seemed to be a gradual “impoverishment” of the small-tomedium sized municipalities, in the absence of the financial support provided by the state budget. The first section of the present endeavor is dedicated to the theoretical challenges and clarifications entailed by the concept of “decentralization” and its actual implementation. Notwithstanding the pertinent criticisms, the present inductive endeavor is set to assess the degree in which decentralization contributed in shaping a new outlook of the local political elite, of the local decision-makers, with a special emphasis on three countries of the region: Romania, the Czech Republic and Poland. Concretely, by employing a positional approach of identifying and analyzing political elites and by operationalizing the concept of “decentralization”, the proposed paper focuses on three case-studies, three small-to-medium sized towns (aprox. 35000 inhabitants), with similar developmental strategies (i.e. the economic dominance of food industry and commercial activities): Tecuci (Galați county), Česká Lípa (Liberec region), and Oleśnica (Lower Silesia voievodship), with the determined scope of identifying, illustrating, and comparatively analyzing, on the one hand, the differences in the administration of communities and the relations with the central authorities (i.e. the degree of de facto decentralization), and, on the other hand, the resulting influences the said differences yields in respect to the outlook of the local political elites in each case (e.g. changes in priorities, in the values embraced, in the perceptions towards the community itself, in the contacts established and the networks of power with other groups and institutions etc.). The populations of the largely quantitative research undertaken are constituted by the members of the Municipal/ Local Councils, in the period 2010-2013, while the research methods employed include: written questionnaire, document analysis, and participative observation. The main contention of the paper is that different levels and different forms of decentralization tend to produce diverging models of political elites, locally.