This paper has two main sections. First, I argue that Hobbes was capable of providing a convincing model of political authority that strengthened the absolutist monarchy, due to two main factors: on the one hand, Hobbes’ conceptualization of freedom, which allowed him to offer a new light upon the relationship between obedience, obligation, freedom and servitude; on the other hand, Hobbes’ redefinition of sovereignty via the concept of representation. I show how Hobbes was aware of the intrinsic tension derived from the attempted convergence of these two distinct logics and I question the kinds of political rupture that are possible under Hobbes’ design, in such a way that would keep a democratic instinct and impulse in political life. After I revisit the relationship between freedom, power and civil disobedience, by looking at the relationship between the sovereign’s and the subjects’ capacity of judgment and by reflecting upon contemporary democratic challenges.