As Tokyo readies itself to host the 2020 Summer Olympic Games, its most infamous postwar red-light district, Kabukicho in Shinjuku ward, has been surprisingly proactive in welcoming a growing number of international visitors: it boasts new large-scale hotels, capsule hotels created for salarymen now reinvented as low-cost options for tourists, and multi-language menus are ubiquitous at local restaurants. A diverse Kabukicho, however, is not a recent development. The nightlife-oriented neighborhood has long been the home of multiple communities stigmatized in postwar Japan, including former colonial subjects cum ethnic minorities, new migrants, the political and artistic fringe, organized crime groups, and precarious workers in its prominent sexual services industry. How might the interplay of multiple marginalities found in a neighborhood like Kabukicho demonstrate potentials and limitations for life in an increasingly diverse Japan? To analyze what this node of Tokyo’s megacity portends for social change in Japan, this paper will extend work in the anthropology, politics, and history of urban Japan to examine how ‘native and newcomer’ coexist in ‘neighborhood’ Kabukicho of the present moment, as Japan grapples with the threat of economic decline due to a rapidly aging society and moribund birth rate, yet speeds toward hosting the world for a second Summer Olympics.