The issue of central railway brownfields regeneration is on the front burner of European cities, also becoming an issue in Prague. Focus of this paper lies in two centrally located railway stations in Prague, Masaryk station and Holešovice-Bubny station, having a long history of plans and projects behind. I identified two forces, lying in the background of most of the projects, forces significantly shaping the way railway brownfields redevelopment projects were proposed. These two forces – the increase of automobile traffic and the need for representation – were used as viewpoints from which to analyse the selected projects of the past, and which can serve as valid viewpoint for the analysis of the recent, contemporary and future projects.