The twentieth century was long, and—despite its best efforts—so were the lives of June and Eugene Gordon. That they were a pairing of a Jewish woman and a Black man alone would have raised eyebrows, but to make matters worse, they were both Communists. Throughout their lives, the pair found themselves confronted by mass anti-semitic and racist violence, state surveillance and repression, and social and financial pressure, which oppressed them through identity and class. Though their personhood and partnership came under assault by legal regimes, backward social convention, and material deprivation, June and Eugene held onto each other and shared visions of a free humanity. These visions were at once profoundly universal and doggedly particularistic. Their intersecting and sometimes diverging paths towards freedom carried them through the life-world of the Communist party, the material and cultural battlefields of the twentieth century, and to one another. The pair’s participation in the labor movement, the Black liberation struggle, and the fight for Jewish freedom spans half a century. Raised in cultures of opposition, they never gave up the fight and took their place in the radical vanguard of civil society, the labor movement, and the literary world. They fought for justice on the battlefields of the Great War, in the pages of Harlem Renaissance publications, the picket lines of the Great Depression, and in the civil rights struggles of the 1950s and 1960s. June and Eugene Gordon’s lives reveal a great deal about the successes and failures of the interconnected Black radical and European revolutionary traditions. Their experiences as activists in the long civil rights movement, as members of oppressed groups, organic intellectuals, and communist cadres provide a unique window into a period of intense political struggle. This struggle brought about a transition in the world history of race, empire, and capitalism, from the era of white dominion to the era of multiracial liberalism. Neither Eugene nor June fundamentally changed the trajectories of the cultures of opposition or political organizations they operated within. However, the length and breadth of their engagement with these oppositional cultures and the Communist movement mark Eugene and June as representatives of a greater whole. They are the Communist everyman and everywoman, fleeting representatives of those who lurk in single sentences within more famous radicals’ memoirs, in brief acknowledgments of their actions or arrest in newspapers, in FBI files, and in the corners of photographs. Through them, we develop a better understanding of the internal workings of the Communist Party of the United States of America (CPUSA); and, more importantly, the conjunctural and organic forces guiding the uneven transformation from the 19th-century world of white Dominion into the one we recognize today.