This essay is meant to analyze how the influential thinker in the history of Tokugawa Japanese Confucianism, Ogyū Sorai (1666-1728), while interpreting the Confucian Classics, made much of “unspeakable” hermeneutic traits and the matters which arose therein. First, having analyzed how he based his scholarship on the study of old phrases and syntax in the Six Classics, the essay then points out that Sorai’s scholarship lay in the pursuance of the compatibility of the “term” with the “things” practiced by the early Confucian sage rulers. The “term” referred to the old phrases written in the texts prior to the Chin-Han period, namely, the language used in the Six Classics; the “things” were the objects the “term” referred to, that is to say, rites, music, law enforcement, and political administration, as noted in the Six Classics. Sorai held that only with the language matching objects it referred to, could one be allowed to discuss the philosophy of the early Confucian sage rulers and Confucius. Second, to explore Sorai’s “unspeakable” hermeneutic traits, the paper expounds (1) Sorai’s emphasis on the “unspeakable rites and music.” The term “unspeakable” here was used to emphasize the dynamic implications for the practice of rites and music. It was far different from the emphasis laid by Song Confucianists on the static implications in the language education on the basis of Neo-Confucianism; (2) Sorai’s use of the term “unspeakable” as a denial of the critical method for hermeneutics advanced by the later Confucians as “out of nothing.” He objected to their interpretation of the Classics via their fictional concepts such as “good human nature,” “divine principles and human desires,” and “inner sagacity and outer kingship.” He was opposed to their random interpretation of the Classics; and (3) Sorai’s own “unspeakable” intention to get rid of the tense hierarchical relations and to downplay the role of Yen Hui, in terms of his purposed, selective interpretation of passages in his A Reexamination of the Confucian Analects (《論語徵》). Last, the paper, based on the above-mentioned analysis of Sorai’s “unspeakable” hermeneutic traits, further points out the paradox formed in Sarai’s method of interpretation and the problems it gave rise to. That is to say, Sorai often nullified his own out-of-nothing principle of interpretation of the Classics and thus confined his interpretation of the Classics to the spectrum of particular meanings, ignoring the universal meaning of the Classics. This possibly stifled openness and innovation inasmuch as the interpretation of the Classics was concerned.