Community-based youth work, through which young people are engaged in community-based educational spaces (CBES; e.g., after-school programs, out-of-school time settings, youth organizations, etc.), is celebrated for supporting youth academically, socially, culturally, and politically. However, when these spaces receive attention, their social and political complexity is often overlooked. Studying the complexity of community-based youth work in education requires interrogating the multiple systems of oppression that impact young people’s lives. It also demands examination of the sociopolitical context of youth work, including how race logics and economic pressures inform the construction of CBES and how these forces surface and intersect with market logics and educational policy reform. Building on existing scholarship on community-based youth work and my current research, I present the youthwork paradox, a framework that captures the complexity of the field and its relationship to structural forces and larger systems of oppression. I detail how this paradox does not always lead to dichotomous discourses; rather, CBES can encompass many logics at once. To illuminate the usefulness of this framework for deeper theorizing of community-based youth work, I ground this concept in an empirical case focused on Black youth workers.