We present a method for the situated discovery and articulation of issues at the intersection between the politics of place making and city planning. We describe the construction and use of designed tools, such as historical political archives; counterfactual maps; and cards to invite situated dialogue between the social and institutional practices and mechanisms that produce our cities. Grounded in an account of the political as vernacular and embodied, our analysis advance understandings on the politics of design, and on the complex interrelationship between places and political spaces. We outline how HCI can adopt methods and develop sensitivities to support democratic practices and publics envisioning their urban futures.