Twenty years after German reunification, surveys have persistently uncovered differences in political trust between the eastern and western parts of the country. Studies have offered disintegrated and inconclusive assessments of the cross-regional variation. This variation is traced to a tenacious, retrospective sympathy for socialism steeped in political socialisation and experiential learning. Empirical analyses confirm the presence of two key effects. First, retrospective evaluations of socialism not only fuel popular distrust of political institutions, but are more strongly correlated with trust in the east. Second, East–West evaluations of socialism are sufficiently different to contribute towards explaining the contrasting levels of trust between the two regions. That socialist values constitute a core axis upon which East German attitudes pivot presents a challenge for nurturing trust in democratic institutions and renews attention to processes through which supportive attitudes to democracy are acquired in transitional countries.