Sovereignty is a paradoxical concept in international politics. On the one hand, conditioned as it is by the distribution of power, it is a relative fact: those states that enjoy military and economic superiority are less constrained in exercising their sovereign prerogatives than less powerful states. On the other hand, as a longstanding norm regulating interstate relations, sovereignty is also an absolute legal fact: states enjoy a legitimate monopoly over the use of force within definable boundaries, which endows them with the power to regulate human relations within their borders according their own criteria. It was this paradox at the core of the concept of sovereignty that led Stephen Krasner (1999) to redefine it as “organized hypocrisy”. The understanding of sovereignty as a violable norm has further made it possible for the development of a set of standards for when foreign interventions in the domestic affairs of states might be justified: i.e. in defense of human rights or in pursuit of international stability. What all this suggests is that when considering the obligations and entitlements of sovereign states, the nature and actions of ruling regimes matter a great deal. Yet any empirical considerations of these seemingly paradoxical effects remain few and far in between. This paper seeks to remedy this glaring oversight by considering the case of the Islamic Republic of Iran, which has often been characterized as an international “pariah” state due to its support for the Shi’a militant organization Hezbollah and its repressive policies at home. Of course, such qualities are hardly unique to the Islamic Republic. Indeed, many other states both in the region and beyond follow similar patterns of behavior (Saudi Arabia, Pakistan, Russia, to name a few). So, why then does Iran especially merit the “pariah” status? The answer to this question, this paper argues, can be found in the paradox at the heart of our normative constructions of sovereignty.