Transition ecologies, namely ecotones, are where life started. Deltas, estuaries, bayous, and wetlands are places where different ecosystems merge and evolutionary processes take place. This paper explores three time periods in four coastal cities to look at the relationship between environmental values and urban expansionist paradigms through reclamation projects. It argues that these thresholds, occurring contemporaneously in expanding metropolitan regions, correspond to changing conceptualizations of urban–nature relationships, in other words urban core's changing relationships to fringe ecosystems. The metropolitan regions used as case studies for this piece are Mumbai, Amsterdam, New York, and Tokyo. Each has used reclamation as a grand expansion strategy during political or economic transitions. During each grand alteration attempt in these regions, the developers, reclamation enthusiasts, or urban planners revisited the city's immediate ecological fringe for expansion, and following these revisitations, a new geographical order formed in their subsequent regions. The urban fringe has become the socio-spatial zone where new and experimental ideas about urban development encounter complex natural systems. The land-use negotiations and reclamation's role in shaping the urban–nature relationships are missing pieces of the planning field. Any future looking climate resiliency plan today should build on the reading of this palimpsest and understand how these environmental values were traded and how global expansion narratives transformed the urban–nature gradient.