Before Guantánamo became what it’s known for — the “forever prison in the war on terror” — its “ambiguous sovereignty” as a U.S. military base was long utilized to incarcerate Caribbean asylum seekers to the U.S. We speak to scholar Miriam Pensack, who researches the history of Guantánamo, in light of President Trump’s recent proposal to once again imprison asylum seekers at the base’s prison complex. Pensack says that existing racist anti-migration policies in the Caribbean, including the Dominican Republic’s detention and deportations of people with Haitian ancestry, suggest a likely collaboration with Trump’s anti-immigrant agenda.