This chapter examines Jürgen Habermas’s Auch eine Geschichte der Philosophie, focusing on the section discussing Rawls, to reveal a structural issue in Habermas’s project of de-transcendentalizing reason. After introducing a more general premise, the chapter reconstructs and critically analyzes Habermas’s appraisal of Rawls’s work (Sect. 1). It then highlights how Habermas’s interpretation of pluralism overlooks the transformative potential of the normativity of ‘the reasonable’ and ‘the most reasonable’ (Sect. 2). This neglect, it is argued, points to a deeper gap: the absence of engagement with Wittgenstein’s alternative approach to postmetaphysical, intersubjective, de-transcendentalized reason (Sect. 3). Finally, this lacuna prompts a closer examination of Habermas’s genealogical framework, particularly the opposition between two pathways—Kantian and Humean—to the postmetaphysicization of reason.