The article attempts first to capture some of the core features of John Dunn's political thought by focusing on his recent idea concerning the  "great dialogue", understood primarily as a means to "globalize the history of human political thinking". It will be argued that Dunn's emphasis on  dialogue derives from his sober understanding of politics as inseparable from the "Cunning of Unreason", a notion coined to reflect the inherent  precariousness and intractability of things political. Recognition of the inevitability of disappointment, according to Dunn, is the first step towards  understanding what we can and cannot reasonably hope. The second half of the article deals with the reception of Dunn's thought in Japan. By  introducing anecdotes concerning Dunn's interaction with some Japanese scholars, a modest attempt will be made to show how Dunn himself is  attempting to put his ideas into practice.