In reflecting upon the arc of these examples, one might argue that, over the last 25 years, urbanization itself has become the preferred instrument of economic production and expression of political power for both established and emerging economies.† However, in contrast to my earlier assertion, many would continue to argue that the decision-making processes and policies that have led to these massive urbanization projects are beyond the traditional purview of design. Yet, when one surveys the examples cited, it is difficult to deny the fact that urbanization throughout history has proven to be a fundamentally speculative act—one characterized by risk, interruption, inflection, and failure (Shiller 2000). And, as such, we must question why the disciplines involved in the implementation of these projects continue to engage the task of planning and design for new settlement with little regard or acknowledgement of the capricious nature of this endeavor. This chapter therefore looks to confront the urban design disciplines’ tendency to treat territorial-scale expansions of settlement as instantaneous, totalizing ventures and proposes to use the increasingly speculative nature of contemporary urbanization as an opportunity to rethink future modes of urban design praxis.