This article examines the encounter of activists from the Anti-Imperialist League of the Americas (LADLA) with African, African American, and Asian anticolonial intellectuals through the League Against Imperialism (LAI), founded at the 1927 Brussels Congress. Drawing from LADLA’s newspaper El Libertador, letters from LADLA leaders, and speeches and resolutions in the LAI archive, it studies how exchanges begun in Brussels influenced debates in radical circles in the Americas. The article builds on extant scholarship and makes two primary interventions. First, it argues that a closer look at LADLA’s participation in the LAI shifts the traditional understanding of interwar Latin American regionalist ideologies, which LADLA rejected in favor of drawing connections to anti-imperialist movements around the world. Second, it argues that the exchange in Brussels influenced LADLA to eventually expand its initial focus on Indigenous struggles to think more critically about Black communities, including Black migrant labor, in political organizing.