This article provides a historical case study analysis of a press system in transition and the role of ownership therein. More specifically, the article looks at early battles over press ownership fought by West German publishing houses in socialist East Germany after the fall of the Berlin Wall. By means of early joint-venture agreements and financial investments, these publishers entered alliances with newspapers long before the latter were officially privatized by the Treuhandanstalt—a semi-public institution responsible for privatizing the entire economy of the German Democratic Republic (GDR). To make this point, the article first sketches some relevant theoretical concepts, then introduces the GDR press system, and finally shows how pre-emptive joint-venture deals became the key to privatizing an entire press system. By uncovering the underlying dynamics of media in transition, this article adds a historical current to the understanding of more recent transformations in media and communications.