This chapter discusses rationality/irrationality and how it relates to a set of either/or (rather than both/and) conceptualizations: the idea of a transition rather than transformations of the Soviet Union and Eastern Europe after 1989/1991 into something essentially different; the idea that Islam has replaced (Soviet) Communism as arch-enemy of the West; the idea of a clash of civilizations between the West and Muslim countries; the idea that religion and politics are separate entities that should not be mixed (like in political Islam). The aim is to explore Swedish media representations of Middle Eastern Islam and (post-)Communism and how they are related to the West over time. Foreign news articles from Swedish newspapers from the last years of the Cold war, via the post-cold-war period of the 1990s, to the post-September 11 period of the new millennium are analysed. In Middle East storylines, religion is recognized as political, while in (post)Communist storylines, politics appears as connected to religious behaviour. Concurrently, both Middle Eastern and (post)Communist countries are represented as connected to pretence, and represented as threats at all examined points in time – the former through an immediate religio-political threat, the latter through a less obvious threat connected to delusion, which might appear as more dangerous due to unpredictability. The continuity of both threats is, however, the factor that stands out the most. Thus there is no either Islam/Middle East or (post)Communism as enemy of the West discourse, but there is a persistent either Islamic/(post)Communist irrationality or Western rationality discourse.