This thesis addresses the issue of urban fracture caused by transport infrastructure, through the design of a tenable, multi-program building with robust structural spans, as well as opportunities for the transient modification or enhancement of its spaces. The site of this exploration is a critical junction in Toronto, where Dufferin Street crosses over the Gardiner Expressway and CNR (Canadian National Railway) corridor. It is the only location in the city where the transport combination of rail and automotive can be described as being “trenched” together. Exhibition Place (south adjacent) and Liberty Village (north adjacent) are among the most contentious areas in the city in terms of their architectural and urban character. The former carries the weight of a rich history in showcase and innovation. The latter is poised to undergo extensive redevelopment in-line with creativity-focused urban policy. The design for this thesis reacts to the enormity of the fracture, which bisects the city from its waterfront, by embracing a need for large span with the spirit of an inhabitable bridge and elevated promenade. Evolving from mid to late twentieth century discussions about megastructure, this thesis examines the notion of ‘building big’ today. It will also examine local patterns of public-private-partnership, posit about the influence that large-scale civic, commercial, and ludic inspired facilities might have on urban communities, and explore scale-determined tectonic and construction logics.