Throughout the late 20th century, urban buildings around the world have repeatedly lost their unique reason for being. The phenomenon of diminished value, while tragic at the time, provides extraordinary opportunities for future use, by offering an authentic narrative to build upon, and overcoming the "blank slate" approach of traditional design thinking. A current generation of designers is recognizing the potential value in these deteriorated and neglected structures and districts. However, we should look critically and creatively at the past to understand the causes of displacement, before attempting to design for the future. War, deindustrialization, tourism, gentrification, white-flight, and economic instability are some of the principal forces responsible for the emptying our downtown communities. By establishing proper analytical and imaginative lenses through which to examine unique developments around the world, we can better see how to reconstitute value in these derelict buildings, thus achieving a more sustainable future. This thesis applies a framework for interjecting creativity and considerations into the regeneration process. I will use a district of abandoned building in the Portland neighborhood of downtown Louisville, Kentucky, to depict these ideas at a variety of scales. This process will develop and utilize appropriate design principles and proposals, to illustrate how architecture can revitalize and reoccupy abandoned buildings, while bringing neighborhoods and communities back to life. In utilizing neglected but rediscovered space, urban infrastructure and buildings within the urban fabric, opportunities are created through the understanding and appreciation of existing contexts, combined with the integration of innovative approaches. The process of uncovering and providing alternative interventions strategies is not linear and blurs the edge between re-search and design. This thesis reveals how architects, by uncovering the past, can fuel a creative process and lead the transformation of a lost community.