ABSTRACT The paper challenges the general perception that the positive–negative freedom discourse privileges negative liberty. It demonstrates that Constant and Berlin’s dual freedom conceptual scheme contains the blueprint of a modern concept of positive freedom and it reveals the nature of negative freedom in an entirely new light. Constant’s ancient and modern liberties have many similarities with Berlin’s two concepts of freedom – positive and negative. The paper shows that these similarities warrant a parallel study and allow us to examine (...) the relation between the two sides of the freedom dichotomy by using the compound terms modern/negative and ancient/positive freedom. It is argued that understanding the relation between the two freedoms depends on accepting ancient/positive liberty as practiced by the participants of modern revolutions. Then we can see why this freedom can both violate and complement modern/negative freedom. The paper argues that the combined tension and mutual dependency of the two freedoms can be explained by tapping into a metaphysical study of human agency, where metaphysics is understood as conceptualisation of moral experience. This helps demonstrate why Constant’s modern liberty and Berlin’s negative liberty rely on satisfaction as a key category reflecting individuals’ capacity for subjective judgement. (shrink)