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Most often, realism (or “Realism”) is spoken of as a political philosophy or theory that places power at the centre of human affairs, or as one that thinks of the ethics of the political realm as distinct from that of apolitical and nonpolitial realms. It has a reputation for being pessimistic—that is, for seeing and expecting the worst in and from the world and its aspects (individuals, states, institutions). However, its self-ascribed endeavour—or at the very least its own nominal claim—is that it describes reality. This article establishes that since realism was formalised in the twentieth century, post the Kantian renunciation of the pursuit of the knowledge of reality itself, the description of reality was interpreted as the ability to navigate the world effectively; that was the realistic approach to take in a world in which metaphysics took a backseat. It contends that it was thus, albeit anachronistically, possible to apply the realist label retroactively to figures like Thucydides, Kautilya, Niccolò Machiavelli, Thomas Hobbes, Friedrich Nietzsche and Carl Schmitt (to name a few) even though these authors perceived reality radically differently from one another and from a Hans Morgenthau or a Reinhold Niebuhr. Finally, it concludes that different epochs have afforded realist authors varying levels of epistemic certainty, and that the epistemic pluralism of the present moment demands that a good contemporary realist be able to work with a highly conflictual political space of appearances and be committed to recreating a shared groundwork within it.