The paper presents a study of Italy’s OSCE Chairmanship in 2018, in particular how Italy is trying to navigate its OSCE priorities while complying with its own political interests. In 2018, Italy received a chance to check whether it can play the role of a mediator in the dialogue between the West and the East. The focus of the article is within a comparative analysis between the Mediterranean region and Ukraine, prioritized in Italy’s agenda for 2018. What is interesting here is how much the statements about maintaining peace and security in Europe could have been and are realized given that some of the OSCE participating countries – Italy and the Russian Federation – were in preparation for elections in 2018.