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This essay compares Lani Guinier’s arguments for cumulative voting with those made by Civil War Era Pennsylvania Senator Charles R. Buckalew. Guinier, an influential legal scholar and civil rights attorney, while Buckalew was arguably the most knowledgeable American of his time on electoral systems. Guinier advocated for cumulative voting to advance representation for minority communities, especially racial minorities. Buckalew, who opposed the Fifteenth Amendment, advocated for cumulative voting to support the election of white representatives given the large numbers of newly enfranchised African-American men. Yet despite their diametrically opposed political objectives, Buckalew and Guinier offer strikingly similar arguments for cumulative voting. They both argue that the single-member district system presents significant representational deficiencies that tend to isolate otherwise self-defined constituencies. Both thought that cumulative voting was consistent with American political thought and values, and its adoption would present no significant break from tradition. The essay explores how both Buckalew and Guinier understood the place of cumulative voting in representative democracy, and where their arguments aligned and where their arguments diverged.