The post-war partition of Germany was not only a territorial but also a systemic one. It mirrored the global Cold War division between communism and capitalism, between party dictatorships and representative democracies. Many experts had advocated a slower transition during which the East German currency would continue to exist but would be made freely convertible at realistic exchange rates. Counter-arguments rejected this proposal as impracticable, especially in light of the fact that East Germany lacked the willingness to serve as low-wage country for Western investments. The chapter demonstrates that there remains a profound sense of disappointment, discontent, and loss among many East Germans. One of the great disappointments of East Germans lies with the apparent irrelevance of classical civil liberties such as free speech in the face of unprecedented social insecurity which they have experienced in the market place.