ABSTRACT What pattern of mind is revealed by the increasingly common turn of phrase “I’m not surprised, but I am disappointed”? Three thinkers who though very influential elsewhere have little cache in contemporary ethical theory—Richard Rorty, Peter Sloterdijk, and Eve Kosofsky Sedgwick—suggest that what they call (respectively) knowingness, cynicism, and paranoid interpretation are endemic to our times. Building on their work, this article argues that knowing confirmation that the (terrible) way things are trending is what we expected all along has a deleterious effect on moral judgment. A knowing lack of surprise, which positions the speaker as savvy, weakens the judgment that follows. If what happened was expected, then the sense that something else could have happened is undercut. Against this mindset, the article synthesizes Rorty’s emphasis on hope with Sedgwick’s on affect, discussing political hope as a virtue with a significant affective dimension to be fostered.