Cites are in a constant state of flux. The progression of time through the centuries has yielded numerous examples of entire transformations of a given city's economic, environmental, social, and cultural structures which in turn shape the physical city. In some instances those structures are allowed juxtapose themselves against each other creating a beautiful palimpsest. In other instances those layers are lost due to the changing forces of the city. As a result the narrative and the image of the city is lost. Where this is most applicable is in the context of shrinking cities. This thesis proposal will seek to explore ways in which the retention of a city's physical history and its memory can be reconciled within the context of a shrinking city. It will question, challenge and hopefully transcend current themes in historic preservation and adaptive-use taking a critical approach toward structures and systems that have lost their reason for being. The testing ground for this proposal is Detroit, Michigan.