This paper studies the critique of Friedrich Hayek’s liberalism delivered by Raymond Aron, on a period that runs from the 1940s to the early 1980s. Through a cross rereading of the main texts of these two twentieth century philosophers, it tries to show that their oppositions—on the place of economic freedom, on the definition of freedom, and on the conception of democracy—reveal the existence of two deeply divergent paths within contemporary neo-liberalism: one that is based on an obsessive attachment to the market and that is accompanied by a pronounced distrust towards democracy; the other that is, on the contrary, built on a trust in democracy, considered as liberalism’s endpoint, which leads to the non- absolutization of the market. Reconsidering this opposition may facilitate a process of moving away from a narrow and caricatural perception of neo-liberalism, which reduces it to a locking of political possibilities.