This study offers a multifaceted perspective on the history and theory of North American urban development. It extends a framework that deconstructs the complex urban evolution process into the three stages of assembly, disassembly, and reassembly. Urban development is explained through planning, architectural and critical theoretical perspectives. This study examines the inextricable links among land use regulations, public policies, transportation, urban economics, and communication technologies and underlines their impacts on shaping suburbia and downtown redevelopments. It argues that today’s revived traditional cores and medium-to-high-density mixed use developments are not mere incarnations of historic urban models. Despite responding to certain real-market demands for livable and vibrant urban environments, these quasi-traditional developments are driven by globalization forces and facilitated by cutting-edge technological advancements. Using combined evidence from theoretical investigations and interviews with experienced professionals, this research demonstrates the complexity and multidimensionality of urban development processes that require in-depth understanding of current global socioeconomic and technological transformations.