Reconstruction-era diplomacy with Caribbean nations was filled with racialized motivations and imperialistic problems. Frederick Douglass—unsurprisingly—found himself embroiled in some of the more controversial incidents. Prior to official postings, his overseas experience generally involved fundraising and promoting transatlantic abolitionism with European sympathizers. As a U.S. official in the Caribbean, Douglass undertook a diplomacy of Blackness, negotiating as a Black man within a white American-dominated system to realize mutual interests of Black people across the Atlantic world. His diplomacy was an important symbol of Black achievement and remains an indispensable subject for U.S. diplomatic historians and scholars of Diasporic and African American…