The Case of the Brownie is an exploration of historical and current events framing the perception of Black masculinity in the context of racial stigma and societal expectations. The book includes narratives to illustrate complex topics related to trauma, aggression, incarceration, apathy, as well as, systematic oppression. Each chapter examines a topic such as trauma, in relation to historical events which have created an adversarial relationship between Black males and mental health or school systems. Discussions concerning overincarceration, increase in suicide, violence, addiction, among other ills continues to be a focus point, without any tangible solutions. This book is written for the social worker seeking a better understanding of how to treat Black males and the mother attempting to support her son. It provides a necessary alternate perspective to police officers and teachers to develop solutions that destroy the school to prison pipeline. The Case of the Brownie is for any reader interested in understanding the effects of trauma on Black males to advocate for transformative solutions, whether in a household, school, church, sports team or prison.