This article aims to shed light on some core challenges of liberating social criticism. Its centerpiece is an intuitively attractive account of the nature and difficulty of critical social thought that nevertheless goes missing in many philosophical conversations about critique. This omission at bottom reflects the fact that the account presupposes a philosophically contentious conception of rationality. Yet the relevant conception of rationality does in fact inform influential philosophical treatments of social criticism, including, very prominently, a left Hegelian strand of (...) thinking within contemporary Critical Theory. Moreover, it is possible to mount a defense of the conception by reconstructing, if with various qualifications and additions, an argument from classic—i.e., mid twentieth-century—Anglo-American philosophy of the social sciences, in particular, the argument that forms the backbone of Peter Winch’s _The Idea of a Social Science_. Winch draws his guiding insights from the later philosophy of Wittgenstein, and one of the payoffs of considering Winch’s Wittgenstein-inspired work against the backdrop of Hegel-inspired work in Critical Theory is to contest the artificial professional strictures that are sometimes taken to speak against reaching across the so-called ‘Continental Divide’ in philosophy. The larger payoff is advancing, by means of this philosophically ecumenical approach, the enterprise of liberating social thought. (shrink)