In a 1944 Pittsburgh Courier interview, African American baseball player Willie Wells stated that he experienced better living and working conditions while in Mexico, citing improved access to accommodations and a warm reception from the Mexican public. From 1910 to 1950, hundreds of black baseball players like Wells defied Jim Crow and walked out on segregated baseball to play in Latin American and Caribbean leagues. Ballplayers like Wells critiqued segregation by framing Latin American nations as counterpoints to segregated baseball in the United States. They commented on interracial games with white major leaguers, their celebrity statuses among Latino spectators, and the social positions that men of color occupied in nations like Cuba and Puerto Rico. Ballplayers conveyed these observations to sportswriters in the black press who used the athletes’ stories to explore the larger socio-political ramifications of their journeys. The story of black baseball in the early to mid-twentieth century was never confined to the Negro Leagues but rather as part of a broader transnational circuit of black and Latino athletes in the African Diaspora. Widening the scope of analysis in this case complicates stories of national integration while centering the voices and experiences of baseball’s racial pioneers prior to Robinson.