Through etymological interpretations and a study of architectural roots, this thesis will propose a modern intervention to a historically rich component of Toronto’s urban fabric. The dichotomy presented between the grounding truth of the authentic and the fleeting temporality of the modern in architecture will play a key role in developing a program and contemporary intervention to the Toronto Central Prison Chapel. Located in the highly developed east end in Liberty Village, this thesis will propose a design strategy that will link Toronto’s founding architectural language to the ever changing needs of the modern individual. The proposed design will serve as framework to embrace the collective and cultural past of the city while preserving and adapting the Prison Chapel to suit contemporary needs of the residents of Liberty Village.