The initial source for the continuous reproduction of contradictions in the central area of New Belgrade’s urban development was the mismatch between the dynamics of political and economic reforms and the static urban planning system that has been banded to the most progressive but rigid functionalist ideals that could not adapt to the emergent pace of these reforms. Consequently, during the socialist and post-socialist periods, the central area of New Belgrade grew irregularly by developing contradictory fragments rather than totality. The inconsistency of the socialist authorities in completing the capital city according to the urban plan despite political imperatives has continued with the post-socialist governing tendencies towards irregularity, privatization, and commercialization of urban development. A series of individual, short-term, and profitable urban projects that have opposed the socialist urban structure, have reused inherited socialist urban infrastructure as a fertile ground for their growth. More than presenting a new insight into the history of urban development of the central area of New Belgrade, this study uses it as the prime case to disclose the unsustainability of the urban planning system during the socialist past and post-socialist present. An alternative urban planning system would embrace the challenges of the continuous reproduction of contradiction by affirming an institutional network of platforms for collaboration among citizens, urban planners, authorities, and developers.