The purpose of this study was to use an appreciative inquiry (AI) theoretical research perspective and change methodology to transform the working relationships and cultural expectations of members through the discovery of their positive core leading to an optimistic and confidence-based future for an urban drug court. This study describes how participants through their participation in the first two stages of an AI 4-D cycle (Discovery and Dream) transformed their working relationships and organizational culture. Participants included an urban drug court magistrate, manager, and purposively selected staff [15 participants]. The urban drug court is designed as a last chance opportunity for substance abusers. As a result of participation in the appreciative inquiry process, participants (a) discovered a resiliency and willingness to overcome challenges, (b) reaffirmed a sense of purpose in their work and (c), discovered a positive core of successful experience. Our study demonstrates the creative possibilities when applying AI to groups mired in deficit thinking. In doing so, we advanced the research in AI, positive organizational psychology, and learned optimism. (Contains 2 figures.)