This article aims to examine the dominant ways of reflecting masculinity by resisting sociologically determined Strongman symptoms across neo-liberal societies. It is divergent from the constellation of gender conflict in Korean society, in that it refuses to reduce the Strongman symptom to the dichotomies of gender. In order to re-articulate masculinity in terms of dialectics of individual and society, it utilizes critical theory and psychoanalysis appropriated by historical materialism, which tried to analyse the emergence and cultivation of authoritarian personality in fascist Germany and liberalist USA. In addition, it analyzes theoretical and political problematic to reveal neo-liberalist psychotic economy to threaten the symbolic sujectivation/subjection for making individual to choose freedom and asks to combine it with the understanding of masculinity as a terrain which the antinomy of individual and society is conducted.