The Treuhandanstalt and trade unions were often perceived by the general public as polar opposites in the economic transformation processes of eastern Germany. Buoyed at first by a rapid rise in membership numbers, union representatives attacked “neoliberal privatization measures” in the media, whom they held responsible for “selling out”, mass layoffs, and the failed integration of East Germany. The federal government and the Treuhandanstalt emphasized, in return, the economic inefficiency of the GDR’s planning bureaucracy, which they claimed prevented any smooth transition to the social market economy. Beyond these stereotypical attempts at passing on blame, the relationship between the Treuhandanstalt and the trade unions was in fact marked by a complex mix of cooperation, conflict, and compromise. This study seeks to ascertain whether one can establish different phases in the relationship between the Treuhandanstalt and the trade unions and, if so, what conditions led to such changes. The relationship between these actors will, moreover, be viewed within the context of the political culture of transformation. The analytical focus lies here on aspects including communication cultures and structures, public discourses, statistical practices and academic expertise, experiential spaces (national-regional-local/east-west), trade union cultures and the debates and conflicts within them. The study will also look into the role played by trade unions in the social and job market policies of the Treuhandanstalt. This constitutes an area that had previously been overlooked in the shadow of the agency’s (more controversial) privatization policies, even though it is of great historiographical relevance in regards to placing the Treuhandanstalt within the (unified) German society in the midst of transformation.