New technologies will inevitably form part of any Caribbean future. Yet technocratic solutions are unlikely to free communities from the political limitations and capitalist entanglements that produced them or answer the question of “Where do the spirits go?” (Rytz 2018). It is then more promising to envision and enact long-term political practices that no longer conceive of emptying islands but rather archipelagos of possibility where memories and futures already reside. This opening recalls artist Jean Michel Basquiat’s rarely discussed text, 50 Cent Piece (1983).[9] In this demanding work, Basquiat examines the pitfalls and paradoxes of sovereignty in the Caribbean in three island contexts—Haiti, Puerto Rico, and Jamaica. To call attention to the limitations of both colonial and nationalist sovereignty, Basquiat links and crosses out various terms including the names of iconic national figures Marcus Garvey, Toussaint L’Ouverture, and Luis Muñoz Rivera. Equally relevant, through explicit references to the US invasion of Haiti, Operation Bootstrap, and Garvey’s Back-to-Africa movement, Basquiat denotes the “collective memory of an ongoing history of violence,” which points to the devastating impact of a specific sovereign power in the Caribbean: The United States (quoted in Negrón-Muntaner and Ramírez 2017, 358).