This essay examines the debate within the community of Black intellectuals and politicians about whether or not to abandon the Republican Party in 1916, and discusses both major parties’ attempts to cultivate Black voters. The objective of this article is to analyze 1916 through the lens of the rise of Black political independence and to elucidate the strains of thought that pushed an increasing number of Black thinkers—and, later, everyday Black voters—to operate outside of the political framework of the Republican Party. Though the momentous shift in the Black vote had not yet fully materialized, 1916 saw a pivotal and significant crystallization of discontent with the GOP that pushed Black voters to search for alternatives, including the radical option of a “Negro Party.” Ultimately, this new sense of political opportunity helped create the atmosphere that allowed Black voters to shift to the Democratic Party from 1928 to 1936.