The fall of two evil systems, Bolshevik Communism in the Soviet Union and Apartheid in South Africa occurred almost simultaneously in the early 1990s holding deep and uncertain implications for international politics. For South Africa, it paved the way towards ending a longstanding hostile international isolation and brought normalisation of diplomatic relations. For Russia it meant the end of Communism but the rise of Putinism. Gerrit Olivier, South Africa’s first ambassador in the new Russian Federation (1991-1996), tells the story of the enriching events in Moscow as he experienced firsthand during his term: the fall of the once powerful Soviet Union; of Soviet Communism; President Mikhael Gorbachev but also of the Cold War and the resurrection of Russia under Putin.