Lisa Tessman (2016: 164) recounts the case of a Jewish mother, running from Nazis, who faced a terrible choice. She could (a) drown her infant, or (b) accept the virtual certainty that her baby’s cries would doom the refugee group she was fleeing with. Given those options, (b) is worse. If the whole group is discovered, many will die, including the infant. Still, preemptively drowning a baby—indeed one’s own baby—is a terrible act. To make sense of cases like this, Tessman (...) turns to the concept of moral failure: an act that violates an important moral value such that the loss cannot be fully redeemed by gains elsewhere. I will argue that criminal justice needs a moral framework like Tessman’s. It needs to make sense of the fact that some options are genuinely better than others, without letting honorifics like ‘justice’ obscure the equally important fact the best available option might be terrible. More specifically, I will argue that when punishment involves prison, as it often does, it is a moral failure. It can be justified only in the sense that preemptively drowning an infant can be justified: like the fleeing mother, society might on some terrible occasions find itself with no better alternative. (shrink)