This chapter connects Shklar’s work on the history of ideas in the 18th century with her skeptical radicalism and her re-articulation of liberalism. It traces another phase in her polemic against anti-modernity through her reading of both Rousseau and Hegel as Enlightenment thinkers who brought the Enlightenment’s own weapons against itself. Much like their work, Shklar’s studies on these two authors are acts of resistance against the politics of abstraction and stereotypical and simplistic readings of that period. Her work on Montesquieu and American political thinkers further successfully challenges the view of the Enlightenment as mindlessly optimistic, coolly calculating, and intent on remaking humanity. Against these ideologically fraught readings, Shklar pitted her authors’ complexity and their ability to bring psychological insights into their reading of the human heart. The chapter suggests that on her personal, idiosyncratic path in the company of these thinkers, Shklar was able to keep into view the perplexities of some of liberalism’s most perspicuous adversaries: their obsession for inequality (Rousseau), their attention for the embodied dimension of the individual (Hegel), and their active and progressive skepticism (Montesquieu).