The Boston Black United Front (BBUF) was a large meta-organization that stands as a pivotal counterpublic institution in the annals of 20th-century community organizing. This study draws on archival documentation to explore the multifaceted strategies employed by the BBUF, highlighting their innovative use of print media, their dual focus on large and small pragmatic interventions, and their impact on the City of Boston. Central to its classification as a form of counterpublic work, I explore the BBUF’s capacity to hold, process, and engage in discourse around ideological diversity and contradiction. The organization came about during a tumultuous period in Boston’s history, before slowly fading out of existence as members pursued other endeavors, but not without making lasting material impact. Their confrontations with carceral violence, endeavors for economic justice, and efforts to foster community-centered alternatives to oppressive systems form the crux of their legacy. I examine the BBUF’s nuanced position and varied roster, inspired by but not fitting neatly into the broader Black Power movement, and emphasize the breadth of their work. This study positions the BBUF as a model for both contemporary activists and planning scholars, illuminating the pathways of grassroots movements in challenging and reshaping cities.