Defeat in the Asia-Pacific War not only marked the end of militarism and the collapse of the colonial empire for Japan, but it also brought into question a modernity based on abandoning Asia for the West. Dealing with this failure was straightforward to the extent that it involved imagining the postwar era as one of revamping earlier modernization through the adoption of pacifism and democracy and the eradication of residual feudal elements within the Japanese system. However, this chapter argues that what this postwar vision lacked for many years was consciousness of a more debilitating wound in need of repair: namely, Japan’s ruptured relations with Asia. Progressive Japanese intellectuals and activists were among the first to face this so-called Asia problem. Their intellectual journey, documented in this chapter, is interesting because it involved facing the fact that their own mentalities were constructed around assumptions of intellectual, civilizational, and racial superiority towards fellow Asians. Exposing and expunging such mentalities—in other words, deimperializing themselves—would become a major project among progressives in the postwar era. Deimperialization was deeply traumatic for progressives because, more than a simple process of accusing others, it was about exposing their own complicity in Japan’s Asia problem. But it was precisely through the trauma of facing such internalized prejudice that progressives were able to construct new imaginations of Japan in Asia and Asia in Japan.