Workers in Latin America led by Mexico's Vicente Lombardo Toledano, founded the Confederación de Trabajadores de América Latina (CTAL) in Mexico City in September 1938. As a confederation of unions from Latin America as opposed to the Americas as a whole, the CTAL sought to provide leadership to advance workers' rights throughout the region. To do so, proponents had to negotiate tensions stemming from the diversity of Latin American politics and the personalities of those involved, as well as their relationships with international labor unions and the multi-lateral International Labour Organization. These conflicts, which were ultimately insurmountable, were evident from the confederation's inception. Although the CTAL unravelled by 1963, the confederation provided a space through which temporary alliances facilitated the exchange of ideas and legislative projects that shaped working conditions for decades to come. Based on the analysis of diplomatic correspondence and the periodical literature surrounding the founding of the CTAL, I show that although Latin American labor was unable to unite to overturn the international power dynamics and economic conditions that led to continued oppression, they were active in shaping the terms of their engagement with the global capitalist system.