This essay examines two reworkings of Sophocles' Philoctetes that were written at the same time on the opposite sides of the Iron Curtain. Tom Stoppard's teleplay, Neutral Ground, transforms the ancient tragedy into a Cold War spy thriller. Heiner Müller's Philoktet, though set during the Trojan War, is an even more radical reimagining of the Greek drama. As in Sophocles' tragedy, the action and language of both modern plays centers on the politics and aesthetics of sympathy. Though approaching questions of compassion from different ideological and generic templates, the two playwrights offer a complementary critique of compassion that puts Bertolt Brecht in dialogue with Hannah Arendt.