The purpose of this article is to examine the phenomenon of pathological gambling and addiction from the perspective of writer and teacher A.H Almaas. By drawing on his Diamond Mind approach we trace the origin of addictive behaviors and pathological gambling to narcissistic wounding, which constitutes the loss of connection with the Essential Identity. A phenomenological hermeneutic methodology was applied in the research process in which Penny, the subject of this case study, willingly shared her life journey through addiction. A thematic analysis clustered into 5 themes revealed a link between her experiences of childhood trauma, addiction, pathological gambling, and the manifestation of fundamental narcissism.