Abstract: Since around the end of the Taishō period when the notion of “modern Japan” apparently captured an elusive reality, questions have been raised as to Japan’s modernity, her past and tradition, and what it means to live within and ahead of her. Like their supposed object, the questions themselves were multifaceted and often pontifically abstruse. This presentation examines the thought of Maruyama Masao in a trans-war intellectual context. It attempts to show the underlying elements in the discourse on modernity that were shared between him and some of his contemporaries — particularly among the participants in the “Overcoming Modernity” discourse, the Marxists, and the “Second Restoration” activists. These include their perception of dysfunctional parliamentary politics, crisis in liberal constitutionalism, the challenge of secular pluralism and instrumental reason, as essential characteristics of their time. Despite the understated agreements behind their perceptions of Japan’s modern conditions, a Collingwoodian critique shows that Maruyama and his contemporaries, for equally understated differences in their notion of the “historical,” offered very different intellectual and normative responses to such conditions. Maruyama’s neo-Kantian conception of history was part and parcel of his unapologetic defense of liberal democracy. The final part of the presentation identifies some of the neo-Kantian moments in Maruyama’s construction of the Tokugawa intellectual past and Japanese “Fascism.”