President Obama’s Clemency Initiative resulted in the commuta- tion of 1,696 federal sentences. Despite this achievement, some advocates of a more robust use of executive clemency criticize the initiative as overly bureaucratic, chaotic, and limited. This paper argues that these criticisms stem from a combination of misunderstandings of and disagreements with the Obama administration’s actual goals. Through exclusive and in-depth interviews conducted by the author with high ranking officials from the White House and Department of Justice, as well as publicly available in- formation at the time, this paper shows that administration officials did not envision the initiative as substitute for broader criminal justice reform legislation. Rather, the Obama administration viewed the initiative as a limited, time-specific remedy to help alleviate a particular unfairness: in- mates serving excessively long sentences based on the date they were sen- tenced. Placed in this context, this article argues that many of the aspects of the Clemency Initiative that have been criticized were features neces- sary for the initiative’s success, as defined by the administration. Finally, this article makes recommendations to future administrations that wish to exercise the clemency power as an effective tool for correcting current and future injustices in the criminal justice system.