This discussion focuses on discourses of queer subjectivity, Maroon identity, and their relationship to Caribbean nationalism. A key aspect of my argument here is the idea that both queerness and marronage are marked by complex insider/outsider identity positions that resist and complicate binarist discourses of belonging and unbelonging. I situate them instead as “crossroads identities” shaped through processes of the contestation and refashioning of dominant national cultures. In discussing these complex intersecting concepts and identities, I point to the ways in which transnational discourses marked by an ongoing engagement with the paradoxes and tensions of belonging and non-belonging—potentially offers another framework for the conceptualization and mobilization of these identities. Framing marronage and queerness as transnational offers a useful opportunity to reassess and broaden the ways in which discourses of transnationalism have been applied to the reading of Caribbean cultural contexts.