One of the interesting aspects of Dewey's early educational thought is his apparent hostility toward children's imaginative pursuits, yet the question of why this antipathy exists remains unanswered. As will become clear, Dewey's hostility towards imaginative activities stemmed from a broad variety of concerns. In some of his earliest work, Dewey adopted a set of anti-Romantic criticisms and used these concerns to attack what one might call "runaway" imaginative and emotional tendencies. Then, in his early educational writings, these earlier concerns were augmented by several other factors, including problematic trends in progressive education, new developments in psychology, and Dewey's own educational aims. This analysis explores the roots of these criticisms, and explains how they culminate in the stance on the imagination that Dewey eventually outlined in the early educational writings. Notably, these findings have some important implications for certain prominent contemporary critics of progressivism.