In this thesis I argue that an architecture that selectively intervenes in the aging landscape to provide opportunities for regeneration and mentorship can weaken our societal divisions. I tested this hypothesis in the context of an adaptive reuse, multi-generational, mixed use design for the Bailey Power Plant, Factory 60, and their surroundings: the former R.J. Reynolds tobacco district in my hometown of Winston-Salem, North Carolina. After a close study of the site's history and its urban morphology, I propose a design based on the concept of urban regeneration in the form of reclamation, adaptation, and mentorship established through a system of green infrastructure that weaves existing neighborhoods into new diverse, multi-generational communities, housed within existing but altered architecture.