After four decades of an expanding carceral state, political leaders are increasingly championing proposals framed as smart—rather than simply tough—on crime. Yet as states increasingly adopt progressive reforms like scaling back the drug war, punishment in other respects continues to grow harsher. This article applies the agonistic perspective to explain these contradictory trends. I argue that the struggles of agonists in the penal field, in the context of socio-structural changes, have produced this pattern of reform. In particular, although the conservative Right on Crime movement has claimed much of the credit, recent policy shifts would not have been possible without the long struggle of progressive and moderate actors throughout the past four decades to challenge the punitive status quo. In addition, the emergent alliances between groups with contrasting political ideologies help explain both the possibilities and limitations of reform.