A textbook activity on symbols was intended as thought provoking but instead elicited a confrontational reaction by one student which left Dr. Jackson and the university searching for a response. When the topic spread through the channels within the university, matters got worse. This disguised case examines the lesson, conflict, and aftermath following a sensitive classroom activity intended to promote transformational learning around the concept of the strength of organizational symbols. Authors suggest organizational theory, power and politics, transformational learning, and cultural competence as possible lenses in which educational leaders can examine this case.