John McDowell claims that a 'human' (as opposed to 'animal') orientation towards the world is characterised by a 'deep connection' between reason and freedom. In this thesis, I argue that McDowell cannot make good on this coincidence, since his Platonic conception of rationality serves to bind free reflection in advance. This is a problem both for the 'minimal empiricism' that McDowell aims to secure in his magnum opus, Mind and World, as well as for the ostensibly liberal, anti-scientistic 'naturalism of second nature' that accompanies it there. Ultimately, I argue that the problems that McDowell's thought is subject to can be solved by invoking the philosophy of nature (and specifically, the idea of 'natural-history') which we can find in the thought of the Frankfurt School critical theorist Theodor Adorno. Adorno is, I argue, able to secure the appropriate connection between reason and freedom, and thus what McDowell himself describes as a distinctively human orientation towards the world. Convinced McDowellians should therefore be motivated to, at least in this sense 'become Adornians'. The thought of McDowell and a number of his contemporaries (Brandom, Pippin) is often considered to represent a kind of 'Hegelianisation' of analytic philosophy; my arguments suggest the need for its 'critical-theoreticisation'.