This chapter examines the legacy of the Chicago Renaissance (1910–25) by focusing on the relationship between writers Sherwood Anderson and Floyd Dell. The chapter pays special attention to Dell’s late-life evaluation of Anderson – Anderson died in 1941, while Dell lived until 1969 – and draws extensively from Dell’s papers at the Newberry Library in Chicago, which underscore his hostility toward literary modernism as well as his associated dislike of Anderson. Although in the 1910s and 1920s, Dell was known as a bohemian writer/editor and leftist political figure, in later years, he became more conservative and tended to stress his allegiance to more traditional literary forms – in particular, realism – and to downplay his championship of the “new.” This tension between realism and modernism is evident in Dell’s ambivalent response to Winesburg, Ohio (1919), Anderson’s modernist-oriented portrayal of life in a small, Ohio town. The article also shows how these tensions may be seen in Chicago literature written after the Renaissance and notes that realism remained the dominant mode of representation during the 1930s and 1940s.