Myanmar occupies a special place in Japan’s relations with Asia owing to wartime legacies that have endowed ties with an enduring warmth and benevolence. This chapter interrogates this “special relationship” with Myanmar through three distinct approaches. First, through an historical overview of the relationship post-1988 and the removal of Myanmar’s long-time strongman Ne Win. Second, through an examination of the Japan–Myanmar relationship that identifies the key political actors and institutions that underpin bilateral ties, in addition to evaluating the impact of economic (official development assistance, or ODA, and technical assistance/policy) links between the two countries. Finally, the chapter speculates on some key emerging trends in the Japan–Myanmar relationship and what they may portend. The chapter concludes that the Japan–Myanmar relationship is highly likely to become one of the most important emerging relationships in Southeast Asia. This is not only due to the case-level significance of Myanmar’s current transformation, but also as the lens through which to gauge broader geo-political shifts. In particular this refers to the growing rivalries between Japan and China as they are expressed through interactions with Myanmar, in addition to the rivalry between differing visions represented by such superpowers as to what future trajectory Myanmar should ideally pursue.