By focusing on Eduard Shevardnadze and Anatoly Chernyaev and on their role in shaping the Soviet response to the events of 1989–1990, this chapter links up with studies on the impact of second-level elite groups such as experts and advisors on foreign policy and in preparing the change of Soviet politics under Mikhail Gorbachev. It focuses on the role of Shevardnadze and Chernyaev in the decision-making process and in shaping the outcome of the "October Revolution" of East Germany and the German reunification process. The chapter divides the course of events into three phases and compares Gorbachev's position with Shevardnadze's and Chernyaev's. The first part deals with their position regarding the "German Question" until October 1989. The second part focuses on their reaction to the opening of the Berlin Wall on 9 November. The third part analyzes the developments after Soviet consent to a possible German reunification was given and discussions became heated about Germany's freedom to choose an alliance.