In this paper I will follow the fortunes of this group, led by prominent individuals like W.E.B. Du Bois and Paul Robeson as well as lesser-known figures such Esther Cooper Jackson or Jack O’Dell, in their encounter with the apparatuses of anticommunism. In numerous and often surprising ways, these critics’ political agenda linked Old Left and New through the Black freedom struggle. As individuals whose intellectual work was imbricated with popular struggles against economic exploitation and white supremacy, this group was uniquely situated to offer a critique of the imperial underpinnings of capitalist wealth and racially structured polities. Drawing upon archival research in the papers of Du Bois, James and Esther Jackson, the NAACP, and the National Maritime Union, among others, my discussion will look at the ways that this group was subject to the discursive and physical limitations imposed by the dominant ideological currents of the capitalist bloc, but I will also focus on how anticolonial ideas circulated throughout the Atlantic at conferences, through campaigns, and in publications. Within the United States, McCarthyism’s impact was considerable, but keeping our attention trained to the transcontinental arena reveals its diminishing reach.