Despite his support for the creation of the West Indies Federation in the late 1950s, the anticolonial activist and political thinker CLR James expressed severe reservations regarding the process that led to its creation. While his criticisms are brief, this paper reconstructs a Jamesian critique of the plebiscite as a means of anticolonial self-determination. Situating his discussion of the plebiscite in the broader arc of his political thought from the 1930s to the 1960s, I identify three lines of critique that revolve around broad questions of mass leadership and the reproduction of colonial domination. First, drawing on his discussion of the tragic flaw of Toussaint L’Ouverture’s leadership during the Haitian Revolution, James argued that the plebiscite enabled popular leaders to skirt their responsibility to effectively communicate with the revolutionary masses. Second, James feared that the plebiscite fixed the principle of territorial sovereignty in place in advance of the process of decolonization by tethering popular authority to clearly bound territorial constituencies. Third, by giving the people a simple choice between two options, James worried that the plebiscite would undermine radical processes of democratic self-constitution. Against conventional critiques of the plebiscite as a means of consolidating dictatorial power under the guise of vox populi, James reveals how ostensibly popular political forms, such as the plebiscite, undercut the enactment of popular agency in colonial contexts.