Could the international conditionality determine the outcome of democratization by forming the mode of interrelations between the incumbent government and private media outlets? In this research, I argue that the international environment can create the incentive structures either detrimental or conducive to democracy depending on the empowerment degree of incumbent government and private media outlets. The goal of the research is to explore the patterns of the macro-micro-macro relations leading to different regime types including electoral democracy and competitive authoritarianism. The research design is within-case analysis in the case study of Georgia. I build the game theoretic model and collect data based on interviewing the governmental officials, the representatives of international organizations and private media outlets. I also collect secondary data and trace the process of democratization over the time of 1991-2015.