The 1927 trial and execution of the anarchist immigrants Sacco and Vanzetti in Massachusetts offered a complex and conflicted template through which contestations of the moment—between the working classes and capitalists, certainly, but also between traditional versions of whiteness and mass immigration from southern Europe; between Boston Brahmin women and men; between the competing visions of America as a project of constitutional democracy and as a white, Protestant nation—were projected onto the global stage, leading to protests and riots around the world. This piece uses the psychoanalytic concept of the transference to explicate the ways in which these legal contestations turn into libidinal investments in literary form—with all the phantastic satisfactions and resistances such textual investments entail. It uses focused close readings of four texts responding to Sacco and Vanzetti: Upton Sinclair’s 'Boston: A Documentary Novel' (1928), Edna St. Vincent Millay’s ‘Justice Denied in Massachusetts’ (1927), William Carlos Williams’s ‘Impromptu: The Suckers’ (1941) and John Dos Passos’s 'USA Trilogy' (1938) to trace how the psychoanalytic transference operates to create meaningful, if ultimately unsatisfying, political and juridical positions. It concludes by proposing, briefly, that this literature of the Sacco and Vanzetti case offers a model for thinking about how the literary transference might be effective in bringing about political change.