The African diaspora has been a key concept adopted by artists, activists, educators, and scholars committed to challenging the specific ways in which the marginalization of blackness has operated and continues to operate among Spanish-speaking Caribbeans and their descendants. This essay focuses on a relatively small network of New York roots musicians of Puerto Rican and Dominican descent who nevertheless have a strong impact on the way the concept of the African diaspora is argued for in local musical, educational, activist, and scholarly circles. They constitute a key component of what Rogers Brubaker has termed the “actively diasporan fraction” who seek “not so much to] describe the world as seek to remake it.” This article documents and analyzes these musicians' reliance on the concept of urban maroonage as a politicized permutation of the concept of the African diaspora and a central component of a liberation mythology and pedagogy. I propose that though this mythology and pedagogy often falls into what Brubaker has criticized as a “non-territorial form of essentialized belonging” it is at the same time a mythology that takes into account what Earl Lewis has termed “overlapping diasporas” as well as the shifting borders of diasporic identity that Juan Flores and others have explored—two key factors in the way diaspora is enacted, but that Brubaker himself fails to address properly.