This paper compares the ways in which Michel Foucault and Quentin Skinner’s historical analyses seek to unsettle the limits on present forms of freedom. We do so by comparing their ways of analyzing discourse, rationality and agency. The two authors differ significantly in the ways they deal with these three phenomena. The most significant difference lies in their ways of addressing agency and its relationship to power. Notwithstanding these differences, the historical analyses of both authors seek to problematize the ways in which past thoughts and practices limit contemporary forms of freedom. While Foucault seems to go furthest in this endeavour, a comparison may enrich both lines of historical analyses.