This study focuses on the development of the Japanese colonial empire and the parallel changes in Imperial Japan’s internal political attitudes and sensibilities with particular emphasis on the changes in the political orientations of the Japanese leadership, over the framework of discussion provided by Nakae Chōmin’s “A Discourse on Government by Three Drunkards”. I look into how racial and economic attitudes of Imperial Japan’s ruling elites towards the colonies changed at the metropolitan center, as the main indicator of how changes in the metropolis affected changes in colonial policies, with the main case studies being Korea and Taiwan, with other colonial entities within the empire being mentioned where necessary. My argument is that as the socio-political conditions within Imperial Japan have changed, due to internal and external conditions and developments, the colonial policy has changed accordingly to reflect these changes. I identify three types of elites and appropriate colonial policies, which I call Founding Father Champions, Parliamentarian Gentlemen, and Warlord Champions, which have come into power in succession as the leaders of empire and determiners of colonial policy.