The Baltimore City uprising of 2015 was in part a reaction to the death of Freddie Gray, but also a response to the repression of this current neoliberal moment. The city’s Black citizenry is one which is profoundly impacted by the school-to-prison pipeline, abject poverty, entrenched neighborhood violence, police aggression and hyper surveillance, underemployment, family stress, health issues, and a host of other challenges and manifestations of violence. Considering this, how does anyone provide a message of hope and engage Baltimore’s largely Black population? This dissertation is a case study that explores the activism of one Black man in contemporary Baltimore and his manifold approaches to the strong, social and economic headwinds that continue to blow through the city. It discusses his efforts to educate and empower his children, other Black youth, and the greater community; his parenting and “otherfathering” as activism; and his deployment of love—Black love—as an important and powerful intervention in spaces where there is often a dearth of resources, opportunity, and hope. This study also considers the everyday life and struggles of a contemporary African-centered organic intellectual and the affective labor involved in his pursuit of transformative change in his community and others like it. This includes a lack of support both in finances and labor, among other challenges. And lastly, with the featured activist’s intended audience in mind, this work explores the subjectivity of Black youth in Baltimore and discusses them as engaged witnesses, artists, and resisters in the face of pervasive violence.