Many American and European cities have to deal with demographic and economic trajectories leading to urban shrinkage. According to official data, 13% of urban regions in the US and 54% of those in the EU have lost population in recent years. However, the extent and spatial distribution of declining populations differ significantly between Europe and the US. In Germany, the situation is driven by falling birth rates and the effects of German reunification. In the US, shrinkage is basically related to long‐term industrial transformation. But the challenges of shrinking cities seldom appeared on the agendas of politicians and urban planners until recently. This article provides a critical overview of the development paths and local strategies of four shrinking cities: Schwedt and Dresden in eastern Germany; Youngstown and Pittsburgh in the US. A typology of urban growth and shrinkage, from economic and demographic perspectives, enables four types of city to be differentiated and the differences between the US and eastern Germany to be discussed. The article suggests that a new transatlantic debate on policy and planning strategies for restructuring shrinking cities is needed to overcome the dominant growth orientation that in most cases intensifies the negative consequences of shrinkage.