The central objective of this paper is to understand the form and performance of a city through a spatial network perspective. The study focuses on Bucharest, a city built in distinct historic phases, facing present regeneration initiatives. The paper revisits previous hypotheses of the evolution of the urban grid, based this time on configurational differences and similarities between cities, previously studied by Hillier et al.(2001), Karimi (1998), and Jacobs (1993). On the background of the overall pattern of evolution of the city, this paper investigates the relationship of distinct central clusters: the Civic Centre, major intervention implemented in the 1980’s as a reflection of the political regime, the Historic Core and the modernist Victoriei Boulevard. The results were interpreted in light of the overall usage patterns which show a poor performance of the Civic Centre as a public space, contrasting the lively historic city centre. Recognisable urban clusters were first depicted by metric accessibility analysis. The study also examined visibility conditions and movement potentials. Syntactic analysis of their structures illustrates the functional implications of spatial modelling decisions and allows in the end to objectively question the future development potential aiming at joining together the distinct clusters with minimum change, keeping their distinct identities yet supporting the functionality of the system as a whole.