Certainty is a prevailing posture of architecture—buildings, after all, do stand up. The aim of this proposal is to look at the unprecedented collection of obelisks that network Rome as sites of unstable architectural classification and as a point of departure for an alternative intellectual history of equivocation and uncertainty in architecture. It is at these sites, vestiges of the paradigms of contested regimes and expressions of power, that one of the most pressing legacies of architecture’s certainty is laid bare. The significance of this research is the development of a design agenda that privileges the multiple over the singular, finding an emergent set of priorities in coincidence rather than in conciliation. I propose to redescribe the sites as points of overlapping concern rather than as absolutes, and to develop a set of “equivocal obelisks” that force a collision between the image of architectural certainty and the precarious, equivocal, and competing narratives this certitude collapses.