The article reveals the principal trends of changes in the relationship with the past in the city of Kaliningrad at the turn of the 21st c. It examines how different social groups and institutions – amateur and professional historians, veterans of World War II, museums, and interest groups abroad – were solving the dilemma that emerged in Kaliningrad during the Perestroika period and were trying to choose what was native and what was foreign in the past of the city. The author argues that the active formation of the relationship with the past of the city, especially during the last decade, by those groups intertwines with the efforts to strengthen ties between Russia and its exclave and makes an impact on the Russianization of the city areas and East Prussian cultural heritage.