This article opens a discussion about how temporalities in spatial and legal spheres are interlinked and shape both policymaking and governance mechanisms and resistance practices. Taking a case study from Eskişehir, Turkey, the research examines several urban renewal attempts of a municipality on the same urban lands over two decades that used different laws and policy tools in each case while all of which were annulled by court suits. From a perspective of legal anthropology, the analysis shows the limits of lawfare discussions that remain incapable of explaining cases that cannot be categorized with domination and resistance. Instead of focusing on detecting who wins or loses, the article claims that such complex cases could be understood better by scrutinizing temporal dynamics: how do legal, spatial, and social temporalities intertwine and impact policymaking? More specifically, how does the law's temporality (re)shape urbanization? Even further, what political work do temporalities generate? The article offers Russian‐doll urbanization as an analogy and ethnographic metaphor to examine several layers and endlessness of renewal initiatives within the broader process of urbanization. Studying the revelation of each layer unravels entangled temporalities of law and socio‐spatial dynamics and their consequences in policymaking and resistance.