We examine the interlinked migrations between the Dominican Republic and Haiti, between the Dominican Republic and the Commonwealth of Puerto Rico, and, finally, migrations from these three countries to the United States. The literature tends to draw stark differences between race and racism in the United States and the nonracial societies of Puerto Rico and the Dominican Republic. However, although Blackness is a contextual category, through analyzing how “Black” migrants are racialized using these three contexts, we find that there is a simultaneously global and local derogation of “Blackness” that places Black migrants at the bottom of socioeconomic hierarchies. Further, these migrants remain largely outside of conceptions of the nation, and thus Blackness is constructed as a blend of racial phenotype and national origin, whereby native “Blacks” attempt to opt out of Blackness on account of their national identity. This dynamic is particularly true in the Caribbean where Blanqueamiento, or Whitening, is made possible through a dialectical process in which a person's Whiteness, or at least his or her non-Blackness, is made possible by contrast to an “Other.” Consequently, we argue that immigration becomes a key site for national processes of racialization, the construction of racial identities, and the maintenance of and contestation over racial boundaries.