Abstract. The article analyzes the policy of the Italian Republic in the Mediterranean during the first and second cabinet of Giuseppe Conte through the prism of the “middle power” concept. Relying on the methods of event-analysis and discourse analysis, the author identifies a number of factors that affect Italy’s ability to realize its national interests in the region. Among them, the most important are: the growing contradictions within the Euro-Atlantic bloc (the EU and NATO) on the current regional dynamic and the aggravation of geopolitical competition in the region; the reactive rather than strategic nature of Rome’s politics; the increasing use of “hard power” as a tool for achieving national interests by regional players. The author argues that in these geopolitical conditions, the room for maneuver of a “middle power” is narrowing while the need to “take a side” in current conflicts makes the politics of “equidistance” no longer available, which is contrary to the geo-economic interests of Rome. The collapse of the bipolar system and the evolution of international relations towards anarchy rather than multipolarity led to the fact that at the beginning of the third decade of the 21st century, both the U.S. and the EU have virtually lost a strategic vision of their relationship with the Mediterranean region. Both NATO and the EU demonstrate a growing failure to develop a common view of regional dynamics and a common approach to resolving current conflicts. Under these circumstances, the strategy of a “middle power”, which Italy has been following for several decades, is becoming less and less productive. Maintaining the “status”, “presence” and “voice” in the existing multilateral formats no longer makes it possible to act as a mediator in a dialogue with third countries, since there is no common understanding of both alliances’ (EU and NATO) goals and objectives. And in case such an understanding begins to appear, it is more confrontational than cooperative (like, for example, in case of the presence of Chinese technologies or Russian gas in the European market), which also reduces the possibilities of international cooperation for a “middle power” such as Italy. Besides, these multilateral structures are becoming less and less useful in protecting its national interests. As the events of the analyzed period demonstrated, the alliances’ “crumbling” on all sensitive issues could not help Rome either in solving the migration problem, or in the Libyan settlement, or in the energy problems. A “middle power” used to rely on multilateral dialogue is increasingly being held hostage by the contradictions of states that adhere to unilateral approaches in achieving their national interests. The new era of geopolitical confrontation in the Mediterranean (between the United States, China, Turkey, Russia, etc.) is increasingly reducing the possibility of maintaining a “dialogue with all” and makes a “middle power” “to take sides”. The article contributes to the study of the Italian foreign policy and the analysis of “middle powers’” behavior in the changing geopolitical context of the Mediterranean region.