Borderlands are wider than borders, and people make them so. In cases where two states have successfully extended de facto control until bumping up against each other, and where the populace on each side displays a uniformity of language, culture, ancestry, and allegiance, we speak of borders, not borderlands. Such cases have not been typical of the Greater Caribbean, to put it mildly. Here, relocation and remixing have been the rule rather than the exception, and newcomers have more often sought to duck central state authority than impose it. People have moved to where states could not follow; states have stalemated each other, creating space for people to move. The same seacoasts that give maps of the Caribbean the illusion of clarity have aided the creation of messy borderlands galore-some at the swampy fringes far from the centers of power, others in port alleyways where loyalty, color, and culture refused to align as authorities expected.Borderlands index the disjuncture between states' territorial claims and their effective reach. For that reason, popular initiative and mobility are at the center of their stories. Our optic, I will suggest, has been distorted by attention to those cases and places where centralized investment of foreign capital generated centralized migratory streams:conditions that favored perceptions of racial and cultural distance and discouraged the building or acknowledgment of connections between newcomers and nationals. One might think, to judge by the case studies available, that by the early twentieth century messy borderlands were largely a thing of the past. One might also think that subjugation to powerful employers and marginalization from surrounding societies were typical of the early-twentieth-century experience of Caribbeans abroad. Finally, one might think that the story of pre-World War II Caribbean labor migration was consistently a story of men.