Recent protests by NFL players and other athletes against racism, racial inequality, and police violence towards blacks and other people of color demonstrate the inextricable ties between sports and struggles for racial and social justice. Historical scholarship on the relationship between race and sports has largely focused on the United States, with many historians documenting the African American and, increasingly, Latinx experiences of the twentieth century. There is also a growing network of historians of Latin America interested in examining how race and sport, among other variables, have intersected in the region’s various nationalist battles against colonialism and dictatorship. Of note here is David M. K. Sheinin’s work on Afro-Colombian boxer Antonio Cervantes (Kid Pambelé). With some exceptions, historical scholarship on sports in the Caribbean has been largely disconnected from these broader historiographies or positioned more firmly within a nationalist framework. Historians focused on sports in Cuba, for example, have long favored baseball and the prospects for sports and athletes on the island in a post-Castro era. Likewise, the few published studies that focus on boxing in Cuba, for example, examine the development of the sport in the early decades of the twentieth century with an emphasis on the influence of the United States and the careers of boxers Eligio Sardiñas Montalvo (Kid Chocolate) and Gerardo González (Kid Gavilán). In response to this tendency to silo Caribbean sports history apart from broader historiographical trends, this panel brings together a range of papers that make sports central to our understanding of the intersections of race, gender, and (trans-)national identity in the (Afro-) Caribbean. The first presenter, Alexander Olson of Western Kentucky University, examines the deep and lasting influence of cricket on the Afro-Trinidadian intellectual C.L.R. James, demonstrating that the sport shaped his conceptualization of the intersection of popular culture and political mobilization in the Black Atlantic. The second paper, by Cat M. Ariail of the University of Miami, offers a look at Jamaica’s Olympic debut at the 1948 London Games, arguing that the experience illuminates the role of identity politics in structuring the possibilities and limitations of the island’s managed, cooperative path to decolonization, federation, and independence. Next, Michael T. Wood of the University of Alabama, explores the transnational nature of American football in Cuba, noting that the Club Atlético of Cuba promoted Cuban collective identity, challenged negative stereotypes, and displayed Cuban inclusion in modern North American sport culture. Finally, Christina D. Abreu of Northern Illinois University presents a look at Afro-Cuban boxer Teófilo Stevenson’s Olympic successes with attention to the overlapping intersections of race and ethnicity, gender and masculinity, and sports and politics from transnational and comparative perspectives.