In much of historic preservation work, artefacts are primarily seen as documents of their time and bearing little relevance to how we design buildings and cities today. Consequently, architectural interventions separate the old and new work, unintentionally distancing historic buildings from their evolving context. There are layers of inspiration embedded within an existing site that can enrich architectural creations. The history of architecture is the story of built forms that have been altered and re-created to make space for the continuation of life. This thesis seeks an archtictural strategy that not only complements but also challenges and reveals the history and material character of the original intent, in order to create greater meaning for the historic building. As a hypothesis, the thesis project presents a schema for the conversion of century old public school in the City of Toronto into a contemporary art museum that demonstrates this strategy, arguing that engaging with the existing work can lead to new insights and meanings.