Nakae Chōmin’s A Discourse by Three Drunkards on Government (三 酔人経綸問答, 1887), according to past research, presents pacifism, military expansionism, and neutral diplomacy—through three characters, a Gentleman of Western Learning, the Champion of the East, and Master Nankai—as a means by which the small state of Japan can maintain its independence faced with the imperialism of the West. However, this paper aims to identify these three characters with Chōmin in the past and present, based on a series of experiences that he had over time. It also aims to examine three arguments in this book with the dual structure of self-criticism, which is composed of Chōmin’s criticisms of his own ideas of the past, and also of his own ideas of each period of time. Re-reading the book from this perspective, one can note that Chōmin makes repetitive self-criticisms through the characters and persistently continues the dis-cussion, even to the point of sacrificing logic. Then, one can see that the main theme of the book is formed around how modern Japan should understand and practice liberty, morality and righteousness, and revolution as it journeys toward democracy. The “given rights” proposed after the heated debate of the characters as an alternative to “revolutionary liberty” helps the reader understand how the idea of liberty was perceived in modern Japan, in terms of conflicts and limitations, as well as how the idea was deeply rooted and maintained in discussions of liberalism and democracy in the country afterwards.