The pardon power, often described as a safety valve on the criminal justice system, is in a state of atrophy. Against a backdrop of “tough-on-crime” rhetoric, a systemic devaluation of rehabilitation efforts, and significant racial disparities in punishment, the disuse of clemency means no possibility of exit for those who have transformed themselves while incarcerated. This Note examines the origins, history, and philosophical underpinnings of clemency in the United States, focusing on the delicate balance between executive discretion and accountability. It then considers the structural and political factors that have contributed to the almost total failure of the clemency process in Massachusetts in recent years. The Note argues for the revitalization of executive clemency as a means of achieving optimal justice in individual criminal cases and system-wide, and it suggests changes to the administration of the clemency process in Massachusetts to achieve that end.