America’s experiment with sentencing guidelines has survived more than a quarter century. They began locally and expanded to State and Federal levels. The ideological neutrality of guidelines constituted their strength and staying power. Yet, their success or failure was judged by the goals a jurisdiction had set for its guidelines, which varied considerably. This paper examined the question of whether the sentencing guidelines movement would grow stronger or weaker as the 21st Century began and changes in criminal justice policy inevitably occurred. Sentencing guidelines have been an effective means of establishing sentencing policies and reflect many varied sentencing philosophies. The guideline systems are defined and based on a set of core principles: proportionality, consistency/uniformity, and rationality/transparency in sentencing. These principles seem to be at odds with new concepts of sentencing and corrections, specifically restorative justice. Restorative justice promotes reparation over retribution. The paper discussed the potential incompatibility of restorative justice and sentencing guidelines as either a perception or as a reality. On a philosophical core, restorative justice appears incompatible with guidelines, but when it comes to practical application there is the ability to incorporate elements of restorative justice into sentencing guidelines. Summarizing the future of sentencing guidelines, the most compelling reasons to expect that they will continue to be widely accepted and applied are their adaptability and ideological neutrality. It is of critical importance that the internal integrity of the sentencing guidelines remain intact.