In her new book on the function of cynicism, Helen Small defines a positive role that cynicism can play in the liberal articulation of the very ideals and norms that cynicism affronts. She provides this “strategic cynicism” with a nineteenth‐century lineage including Friedrich Nietzsche, Matthew Arnold, George Eliot, and Thomas Carlyle. This review essay identifies some problems in the concept of strategic cynicism, drawing on Hegel's understanding of intentional action. Strategic cynicism is ultimately a role‐playing (or impersonation) of cynicism by normativity on its own behalf. As Small conceives norms, they are vulnerable to cynicism because they are stranded and without immanent grounding. Turning to Henry James's novel The Awkward Age, this essay shows how cynicism can be answered not by pointing to better intentions, but only by what we discover retrospectively, from the consequences of how things turn out, our commitments to be. The essay ends with a consideration of the dysfunction of liberal responses to Donald Trump's cynicism.