Takeuchi Yoshimi is one of the very few postwar Japanese intellectuals to openly engage in discussions on Asia intricacy and to deal with the most complicated component of the Japan–Asia relationship: problems of emotion. One key feature of Takeuchi’s approach lies in the fact that he is not only a profound thinker but also a sensitive litterateur. For this reason, in addition to the fact that it is already very difficult to form an objective and widely agreed view on Takeuchi and his approach, it is hard to avoid the emotional aspect when evaluating his thoughts. This essay does not aim to discuss his rights and wrongs; rather, it is an attempt to analyze the inner logic of Takeuchi’s thoughts, to understand and grasp the intensity and structure of his thoughts and emotions, and to demonstrate where his sense of urgency lies, thereby allowing to view the examination of the diverse and complex nature of discourses on Asianism in Japan in a new light.