The disintegration of the USSR was one of the greatest management failures of the twentieth century, but is never considered from that standpoint. This monograph uniquely does so, using insights from complexity theory to elucidate the problems Gorbachev faced as "CEO of the Soviet Union" and why he was unable to solve them. In particular, it addresses the question of Soviet organizational learning and draws lessons for questions faced by contemporary complex organizations, including business corporations, such as merger, acquisition, spinning off, and the relative autonomy of subordinate managers. Analyzing changes over time in the Soviet foreign policy making Establishment, this monograph specifies how an actor's interpretation of the environment (in terms of decisional time horizon and experienced stress) evokes differentiated mechanisms that themselves constrain the types of decisions that the actor is able to take in such an environment. It exemplifies those mechanisms with concrete instances of communicational and organizational constraints and freedoms that draw on empirical case studies. From this, it draws lessons for the management, corporate culture, and design of twenty-first century organizations, including business firms of any size.