Historic preservation emerged from the desire to protect buildings of cultural significance. This worthwhile endeavor has evolved to present a narrow path forward that is not sustainable. Buildings deemed historically significant have limited options for repair or reuse, which typically result in a steep financial burden. Over time, such practices cripple the development of a city, leaving it unable to respond to the needs of the community. What would more forward-thinking historic preservation—focused on equity and sustainability as well as cultural significance—look like, in both policy and practice? In my thesis, I explore this question using two primary approaches: reimagining the Bronx Borough Courthouse and reevaluating historic preservation laws. The focus of my proposal is the conversion of the vacant courthouse into a transitional study center for formerly incarcerated people, wherein the architecture itself becomes a manifestation of their transformative journey. This vision is achieved through strategic architectural interventions: push, pull, shell, and frame. I also aim to initiate a dialogue around the need for new historic preservation legislation, paving the way for a more adaptable and inclusive future that addresses the diverse needs of all communities.