Attempting to apply the logic of conflict analysis developed by Thucydides to the chaotic spasms and clashes triggered by the collapse of the Soviet Union might appear inappropriate to many classical scholars, and entirely artificial to most Eurasian security experts. However, the two strategic landscapes, though separated by a period of some 2400 years, share a number of common features, and the ideas of the ancient strategic analyst may prove helpful for discovering structure in the chaotic violence of more recent times. The notion of the 'strategic dilemma' *one that Thucydides never used but is credited with inventing *lies at the centre of this investigation, which seeks to test the applicability of the notion in three distinctive settings: in a bipolar confrontation; in conflict manipulation by a third party; and in secessionist conflicts. The article suggests that, as an instrument of political analysis, the security dilemma tends to overpredict conflicts and essentially comes out as a trap of self-fulfilling 'worst-case' expectations, so that nowadays *much as in ancient Greece *whenever a security dilemma determines a political decision, disaster follows.