This article examines Irving Babbitt's probing critiques of John Dewey's ideas at the beginning of the 20th century. Babbitt (1865-1933) was the co-founder of the New Humanists, a collection of scholars and academics who advocated for a return of the Greek and Roman classics in the American curriculum. Babbitt believed that both naturalism and positivism eradicated any sense of inner-discipline modelled by the classical curriculum. He pointed to Dewey as the embodiment of these strands of the "new" education [Babbitt used this term in his 1908 "Literature and the American College: Essay in Defense of the Humanities" (p. 93)]. Scholars have commented upon the philosophical quarrels between Babbitt and Dewey, but they have seemingly neglected the study of a fundamental belief held by both Babbitt and Dewey [These sources will be further examined in this paper: Beck (1962), Hoeveler (1977), Karier (1986), Kirk (1979), Kliebard (2004), Nevin (1984), Panichas (1999) and Ryn (1997)]. Babbitt shared (and praised) Dewey's cautions and warnings of the cult of specialization taking grip of both American society and its schools at the beginning of the 20th century. These two adversaries found common ground in cautioning what increasing specialization meant for American democracy. An examination of their shared caution, though ultimately unheeded, provides a glimpse into curricular concerns in the early decades of the century, particularly education's role in fostering American democracy. As neo-conservative forces at present seek to replace humanities education with more career-driven fields of study, Babbitt's own conservative voice echoes Dewey's cautions of what such specialization means for democracy from a century away.