In this episode, I speak with Maleek Jackson, owner of Maleek Jackson Fitness Boxing Gym in Philadelphia. Maleek spent 10 years in prison from ages 16-26 and in our conversation, we contextualize criminal behavior, interrogating how, for those in the streets, it is not about “right” or “wrong” but about doing what you need to do to survive with the limited opportunities available. We discuss how chaotic environments, resulting from racist systems and structures, tend to muffle positive messages promoted through community-based programs, mentors, and old heads. Maleek describes the individuals who influenced him throughout his life, for better or worse, and emphasizes the multifacetedness of each individual’s identity. Ultimately, this conversation serves to humanize those so often demonized, complicate deficits-based narratives about those deemed “bad” and provide insights into the influential and often conflicting roles of mentors and environments.