This paper presents a case study of sentencing policy in the adjoining, and demographically and culturally similar, states of Minnesota and Wisconsin. Using administrative data, together with historical and legal analyses of sentencing policy in each state, it (1) argues that the destabilization of the penal order represented a critical juncture during which commission‐based, presumptive sentencing guidelines were an option in both states; (2) analyzes how the decision to adopt this guidelines system in Minnesota and the failure to do so in Wisconsin initiated path‐dependent processes, making it difficult to reverse the initial policy choice; and (3) assesses how these distinct policy paths led to different penal outcomes. A concluding section discusses how analyses of path dependency shed light on the state variation in sentencing policy and provide a framework for assessing the possibilities of, and obstacles to, penal reform.