The last decade has witnessed the spectacular collapse of economies that became too reliant on urbanization as their primary means of economic production. From the ghost estates of Ireland to the artificial oases of Dubai to the sprawl of the U.S. Sunbelt to the unoccupied new towns scattered across western China to the abandoned infrastructures of Spain, speculative expansions of urbanized territories have proliferated in a wide range of economic, political, and geographic contexts (Buckley and Rabinovitch 2010; Campbell 2011; Glaeser 2010; Hardaway 2011; Lewis 2011; Medina 2012; Palmer 2011). I refer to this phenomenon as “The City That Never Was” and contend that it is a fundamental crisis facing contemporary city design and development praxis. As such, it is worth asking what the implications of this reality are for the planners and designers engaged in the implementation of these metropolitan initiatives and, in particular, how confronting this phenomenon might expand the potential efficacy of landscape-driven approaches to urbanization.