In the field of Taiwanese Literary history, Huang De-shi has been seen as a pioneer, an innovator, and one of the first scholars of the colonial era to question how the history of Taiwanese literature ought best be written. His concern for literary history was self-conscious and ongoing, and thus the discursive parameters of his "history of Taiwanese literature" encompassed both the classical and the contemporary periods. To this day, no one has surpassed his treatment of the classical era of Taiwan's literature. This paper seeks to uncover the overall discursive structure of Huang's research through an examination of the ideas and interrogations inherent in his treatment of classical Taiwanese literary history. Related opinions found in his journals will also be considered, especially with reference to René Wellek's (1903-1995) views on the writing of literary history. The intention is to discover how Huang applied principles of multi-layered localism, nationalism, and Pierre Bourdieu's (1930-2002) concept of “field”(champs) to construct his category theory of Taiwanese literature. This in turn helps establish the rhetorical and narrative devices that he employed in explicating the works of various authors. This article also tries to shed new light on a number of issues, such as why he was not able to finish his writing of Taiwanese literary history, and whether it is true that he plagiarized his contemporary, Lian heng's ideas in his discussion of classical literary history.