Of the thirty-odd clemency petitions I prepared this year as an attorney with the NYU Clemency Resource Center, Tom’s was perhaps the strongest. Tom left home at sixteen because his mother, a methamphetamine addict, physically abused him. Out on his own, he began using drugs and was soon addicted, dealing small quantities to support his habit. One night when he was twenty-one, his girlfriend, also a drug user, asked him for heroin. They shot up together; unbeknownst to Tom, she had also taken a large amount of cocaine, and she suffered a fatal overdose. At trial, the jury found Tom guilty of drug distribution, but acquitted him of causing his girlfriend’s death, following testimony she had taken only about one-twentieth a lethal dose of heroin. Notwithstanding the verdict, however, the Judge found that heroin had contributed to her death. He sentenced Tom to eighty years in prison, under then mandatory sentencing guidelines. Tom is no angel, but eighty years for an accident that happened when he was twenty-one seemed wildly excessive. I was not the only one to think so: In a letter of support to the pardon attorney, the judge explained that Tom’s sentence had haunted him since he imposed it sixteen years ago. But despite this strong support, last week I had to inform Tom his petition had not been granted. Understandably, he was devastated. The Office of the Pardon Attorney provides no explanation for clemency decisions, so I was left to give him the same answer I had to give so many of our clients: That, as deeply unsatisfactory as it must sound, the Obama administration’s clemency initiative was often a crapshoot. The initiative shares this quality with federal sentencing in general. Using a quasi-arithmetic formula, the federal sentencing guidelines promulgated by the United States Sentencing Commission produce a time range that forms the basis for federal judges’ sentencing determinations. The range’s odd specificity — 262 to 327 months for many drug offenders with prior distribution convictions, as just one example — lends an almost scientific aura to the calculation. But in practice, depending on the charging decisions made by the prosecutor and the views of the judge randomly assigned to the case, sentences for the same offense may vary dramatically. And, largely because of mandatory-minimum sentences that Congress has enacted, sentences often skew wildly more severe than the underlying crimes warrant, particularly for drug offenses. The clemency initiative was designed to help remedy this problem, by reducing some of the most egregious outlying sentences for certain deserving inmates. To identify these individuals, the administration announced a series of criteria, including that the petitioner be a non-violent, low-level offender, with good conduct in prison and without a significant criminal history, who had served at least ten years of a sentence that would be substantially lower today. Initially, administration officials estimated that perhaps ten thousand inmates met the criteria. Ultimately, however, only about 1700 petitions were granted. For these lucky few — even when the clemency grant shaved only a few years off the initial sentence, or the new sentence remained enormously long (twenty-five years or more, for some grantees) — the Obama administration did an extraordinary thing. But unfortunately, in granting so many fewer petitions than originally projected, the administration may have done more to exacerbate the arbitrariness of the sentencing regime writ large than to remedy it. As became clear over the last several months — during which the majority of the clemency decisions were announced — it was often impossible to find any meaningful difference between the petitions that were granted and those that were denied. One can see how this happened. The administration’s criteria appear straightforward enough, but as every law student knows, a multi-factor test with such nebulous requirements (what does “low level” mean? “Good” conduct? “Significant” criminal history?) will defy consistent application. This would be true even for a single decision-maker; under the much-critiqued clemency process, however, the Office of the Pardon Attorney, Deputy Attorney General’s Office, White House Counsel’s Office, and ultimately the president himself all separately evaluated whether the criteria were met. Along the way, the local United States Attorney’s Office — the same entity that initially prosecuted the applicant — and the sentencing judge could offer their views and any additional information they possessed, without the applicant being afforded the opportunity to respond, thereby risking entrenchment of the same individual biases and regional differences that produced the initial sentence. Running this gauntlet, petitions might easily be declined even though they deserved to be granted. Our experience at the Clemency Resource Center provides some small indication of the extent of the problem. Of the 200 or so petitions we and a sister organization submitted, ninety-six were granted — on its face, a wonderful result. But while each grant was the cause for celebration, as well as for sincere gratitude to the administration, predicting which clients would be successful was impossible. Petitions only a mother (or a defense attorney) would be confident about might sail through the process within weeks of submission. A handful of inmates whom we declined as hopeless — a difficult decision, but one we thought the criteria required — later successfully petitioned the administration on their own. Meanwhile, petitions that clearly appeared to meet the criteria, for clients like Tom with incredibly compelling stories, languished for months, only to be finally denied last week. Still, at least these clients received a decision: Others — for reasons that again appear largely arbitrary — did not. The Obama administration never settled on a clear deadline for submitting petitions. During a conference call with clemency attorneys in August 2016, the pardon attorney suggested that petitions submitted by the end of September would make it through the process; the deputy attorney general, however, later announced that August 30th was the cut off. Last week the administration announced that all petitions received by the earlier date were considered, but almost ten percent of the petitions CRC submitted before this deadline still remain pending. And while the administration ultimately reviewed several hundred petitions submitted in September, heartbreakingly, many deserving clients whose petitions we rushed to submit that month also never received a decision. There is no apparent reason why any of these petitioners was passed over. For the incredible difference it made in the lives of about 1700 inmates and their families, the Obama administration should be heartily commended. I have no doubt that the administration tried to be consistent in the undeniably monumental task of winnowing this elect from the tens of thousands of petitions they received. And, as administration officials stated repeatedly and rightly, clemency could never be an adequate substitute for comprehensive sentencing reform, which Congress failed to pass. But as this remarkable moment has come to a close, with the Trump administration highly unlikely to do anything remotely similar, there is good reason to be troubled by the randomness of the decisions and profoundly saddened for all the deserving inmates left behind, the thousands and thousands whose hopes were raised so high and now have been dashed. Sean Nuttall was a staff attorney with the Clemency Resource Center, a legal-services office founded to prepare clemency petitions under the Obama administration’s clemency initiative, until its scheduled closing in 2016.