This essay focuses on the writings of Charles Chesnutt in order to rethink the expressivist and democratizing assumptions about the market that literary historians in the United States have borrowed from classical economics. In particular, it analyzes the discourse of friendship used to describe the continuous and changing social practices of patronage and philanthropy in the era of corporate capitalism. Such friendship calls into question simple conceptions about supply and demand, consumer preference, and the diversifying power of markets. Placing Chesnutt's writings in dialogue with those of Booker T. Washington, the essay analyzes the African American debate over the significance of corporate capitalist friendship. Chesnutt is, on the one hand, intrigued by the language and possibilities of corporate philanthropy. He works to imagine if such friendship can be linked to an older radical discourse of friendship stemming from the revolutionary era. On the other hand, especially in The Colonel's Dream (1905), he finds himself continually frustrated by what corporate philanthropic friendship evades—namely issues of justice. This essay therefore finally challenges assumptions about “free” markets that we have unconsciously relied on in our literary histories, while also showing how a focus on the social practices of patronage and philanthropy helps us ask new questions about the relation of literature to corporate capitalism.