Democracy and tragedy captured a delicate poise in ancient Athens. While many today perceive democracy as a finite, unquestionable and almost procedural form of governance that glorifies equality and liberty for their own sake, the Athenians saw it as so much more. Beyond the burgeoning equality and liberty, which were but fronts for a deeper goal, finitude, unimpeachability and procedural norms were constantly contradicted by boundlessness, subversion and disarray. In such a world, where certainty and immortality were luxuries beyond the reach of humankind, tragedy gave comfort and inspired greatness. The purpose of this article is to draw explicit links between democracy, tragedy and paradox. Given that tragedy's political ascendancy coincided with the birth of democracy in ancient Athens, we may assume that democracy was somehow, if not implicitly, tragic. But what was it that made democracy and tragedy speak so intimately to each other and to the Athenians who created them? The answer, at least the one which this article entertains, is paradox.