During the Cold War, athletic performances were also political statements. But that was then. For every year that passes since the fall of the Berlin Wall in 1989, the memories from that time seem to become more and more blurred. Of course, there are those who simply do not want to remember, who just want to forget and even erase that period from the collective memory. If we agree that Cold War sports were political in their essence, we may also interpret this fact from different angles. Of course, the most obvious interpretation is to say that Cold War sports manifested the conflict between two economic and political systems, that is, state-socialism vs. capitalism, or communism vs. liberal democracy. This is the most obvious interpretation. But it was also a war between different kinds of gender constructions of the female athletes, and the Olympic Games were the most important stage in which this war took place. From a Western perspective the female athletes of the Eastern Bloc were controversial; especially the East German “wonder girls” of the 1970’s and 1980’s. During these decades athletes such as Marita Koch, Katrin Krabbe, Heike Drechsler and Kornelia Ender dominated the Olympics. Their physical appearances were controversial. In fact, many commentators have reduced them to mere doping cheaters manufactured in state-controlled laboratories. This is a rather common description. But what does it mean to describe them in this way? Well, for one thing it means that they must have challenged – and potentially undermined – the Olympic spirit and Olympic values because they presumably were neither “natural” nor “clean” athletes. In short, they were bad for the Olympic ideal. Of course, this is just one way of understanding the Eastern Bloc sports phenomena. Another perspective is to say that these athletes – and what they stand for symbolically – made important and valuable contributions to the gender debate in sport. More precisely, they showed, through their mere existence, a “different” way of being a female athlete in a heavily gendered and masculine sports world. Often, the Eastern Bloc athletes were outstanding, and it is not a secret that their bodies were partly built by powerful performance-enhancing drugs. They also transcended narrow gender boundaries, partly because of the heavy use of such drugs. In doing so they also transcended the traditional conception of modern sport as a male’s only arena. In this chapter I discuss some of the essential arguments concerning the rise and fall of gender radicalism. Gender radicalism, as I will define it throughout this essay, can be manifested by athletes who act at the edge of gender boundaries, sometimes with the consequence that they transcend these boundaries. In order to make my argument as clear as possible I focus on the polarization between Eastern Bloc sports culture (as it appears to us through the common story of Olympic sports) and Western sports culture. I will show how the mere existence of the Eastern Bloc challenged commonly accepted conservative gender norms. This resulted in an overall improvement of the status of female sports. Another way of putting this is to say that the fall of the Berlin Wall also became the fall of the (last?) serious attempt at being gender radical at the Olympics, and that it also led to the return of traditional and reactionary gender values.