Will existing forms of artificial intelligence (AI) lead to genuine intelligence? How is AI changing our society and politics? This essay examines the answers to these questions in Brian Cantwell Smith's The Promise of Artificial Intelligence and Mark Coeckelbergh's The Political Philosophy of AI with a focus on their central concern with judgment—whether AI can possess judgment and how developments in AI are affecting human judgment. First, I argue that the existentialist conception of judgment that Smith defends is highly idealized. While it may be an appropriate standard for intelligence, its implications for when and how AI should be deployed are not as clear as Smith suggests. Second, I point out that the concern with the displacement of judgment in favor of “reckoning” (or calculation) predates the rise of AI. The meaning and implications of this trend will become clearer if we move beyond ontology and metaphysics and into political philosophy, situating technological changes in their social context. Finally, I suggest that Coeckelbergh's distinctly political conception of judgment might offer a solution to the important boundary-drawing problem between tasks requiring judgment and those requiring reckoning, thus filling a gap in Smith's argument and clarifying its political stakes.