Since the mid-1990s, homelessness has become a major issue of public discussion in Japan, and is often viewed as a new social problem facing Japanese society. The issue of homelessness contrasts images of the absence of poverty and homelessness in postwar Japan, often explained based on the unique features of Japanese-style employment and welfare, containing poverty and unemployment. This paper contrasts these views with a perspective on the continuity of poverty, and homelessness in postwar Japan. Specifically, I discuss the characteristics of homelessness in Tokyo, how they relate to the structure of the economy and employment practices, and how the problems of today's homeless are accommodated in the welfare system. I argue that the homeless cast light on patterns of loss of employment, housing, and means of subsistence, characteristic to Japan's economy and welfare system, and contribute to a new understanding of the dynamics of poverty in contemporary Japan.