John Dewey’s instrumental theory of knowledge offers a starting point for the exploration of new territory in landscape architecture, specifically the gap between intention and reality. This space is always at issue in landscape architectural practice and yet remains largely untouched by contemporary theoretical and technical projects. In recent years the discipline has become concerned and engaged with design issues caused by the unintended consequences of our society’s industrial legacy and rapidly changing ecological and economic realities through the conceptualization of landscapes that can perform multiple functions through time. This paper presents the results of ongoing research that grapples with the gap between intention and reality and suggests that this approach to landscape architecture is an appropriate and promising disciplinary response to extreme and changing conditions. It does so first through a critique of current theories and then proposes new conceptual and technical tools for analysis and representation through a speculative project for an industrial shipping canal landscape on the edge of the Rio de la Plata Estuary in the heart of Buenos Aires, Argentina.