This chapter examines Brecht’s complicated relationship with the German Democratic Republic and its leaders.In 1948, after the end of World War II, Brecht returned to Germany and ultimately settled in East Berlin in the GDR, where he became the artistic leader of the famous Berliner Ensemble, the most influential postwar theater group in the world. However, because of his revolutionary approach to drama and aesthetics, Brecht quickly ran into conflict with East German leaders and had to endure a series of criticisms and accusations against himself and his artistic collaborators. Brecht also sought to democratize and liberalize the artistic and cultural sphere of the GDR. Ultimately, Brecht’s relationship with socialist leaders in the GDR represented a push-pull and give-and-take. Each side had to compromise, and each side received something in return. Brecht received his own theater and the ability to perform plays as he wished, while the leaders of the GDR were able to bathe in the glory of Brecht’s international artistic success.