This article develops an ideal of sentencing discretion as consisting in sufficient dispositional flexibility for the trial judge to set, on behalf of the polity, reasonable terms for the continuance of relations with the offender in view of his crime. This ideal requires trial judges to have what may be termed “substantial” sentencing discretion: discretion that is exercised with direct reference to the values and goals penal sanctions are expected to serve, and where it is this quality of value-based engagement that provides the justification for the decision. The article engages with empirical research into sentencing that helps us address the strength of the case for and against substantial sentencing discretion, and ultimately defends substantial sentencing discretion on functional as well as ethical-political grounds.