Beginning in the late 1990s, a debate emerged whether Edmund Burke might be read as a significant critic of empire because of his impeachment of Warren Hastings. The debate that ensued, I argue in this article, revealed ambiguities and paradoxes in the category of anti-imperialism. Rather than imperialism and anti-imperialism representing a clean binary, anti-imperial projects, events, and figures may embody the very sorts of politics that many disciplinary debates about anti-imperialism wish to critique. Foregrounding “anti-imperialism” in the history of political thought, I conclude, may obfuscate as much as it illuminates—even when examining the twentieth-century experience of decolonization.