What Compassionate Release Might Have Been
An attempt at a compromise at the U.S. Sentencing Commission failed. Now, the Supreme Court will decide the years-long fight and the scope of the Commission’s authority
This is the second in a series of essays about sentencing and corrections law cases on the Supreme Court’s docket in the upcoming October 2025 term.
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I had the great privilege of representing the Attorney General of the United States as a non-voting member of the U.S. Sentencing Commission for about ten years. I served five different Attorneys General over that time. A few of the AGs had a keen interest in sentencing law and policy. About two months after taking office in 2009, with just a little nudge from a few of us in the Criminal Division, Attorney General Eric Holder issued a memorandum to the heads of all Department of Justice components and all U.S. Attorneys announcing the formation of the Attorney General’s Sentencing and Corrections Working Group.
The Department of Justice is committed to ensuring that our sentencing and corrections systems promote public safety, provide just punishment to offenders, avoid unwarranted sentencing disparities, and reduce recidivism by breaking down barriers for ex-offenders to successfully rejoin society. We are also committed to addressing the disparity in sentencing policy between crack and powder-based cocaine offenses.
The Working Group would, over time, lead to policy changes on charging and sentencing advocacy, prisoner reentry, racial and ethnic disparities in sentencing (including federal cocaine sentencing policy), diversion and other alternatives to incarceration, and the Department’s death penalty review protocol. It also led, in part, to Attorney General Holder’s Smart on Crime Initiative in the Obama second term and with it, lots of other reforms.
Attorney General Jeff Sessions also cared deeply about sentencing, but from a somewhat different perspective. In the summer of 2017, a few months after he took office, he and I had an extraordinary and wide-ranging conversation about sentencing law and policy. He knew the Guidelines. He knew the Commission. He knew about Attorney General Holder’s Working Group. He expressed with certainty that prison worked to reduce crime and that he wanted the Guidelines tougher. He was well-aware of Judge (and then-Commissioner) William Pryor’s proposal to restore presumptiveness to the Guidelines that he laid out before the American Law Institute. Pryor had been Session’s deputy in the Alabama Attorney General’s Office years before. But despite that, Sessions didn’t really care for Pryor’s proposal and the dramatic changes it would have made to federal criminal procedure.
A few days after our conversation, I received a call from the Deputy Attorney General’s Office, relieving me of my position on the Commission. I would only return to the ex-officio role after President Biden was inaugurated.
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Representing the Attorney General on the Sentencing Commission is less about expertise in sentencing law and policy and more about navigating policy and political crosscurrents, internal and external to the Department of Justice. There are many stakeholders that care deeply about federal sentencing policy, often with very conflicting views. The goal for the Attorney General’s representative, at least as I saw it, was to try to shape and work towards a just policy outcome that the Administration could support and that would be sustainable over time. The means to achieving that goal were mostly diplomatic; the job was mostly one of diplomacy.
Over the years I served on and around the Commission, many of the other commissioners and the Commission staff, while largely polite to me, were quite unhappy that only one of the parties to federal criminal cases was at the Commission table. Just under the surface, but never completely hidden, was quite a bit of resentment. The Department of Justice is seen there mostly as an advocate pushing parochial and knee-jerk punitive positions, not a collaborator in search of justice for victims, defendants, and the public alike. And if one of the parties to federal criminal cases is at the table, they surmise, shouldn’t the other side be there too.
Sometimes the Department’s policy positions before the Commission have indeed been punitive. But sometimes not. Sometimes they are blurry and malleable, at least in the details. Sometimes the position is quite inflexible. When, during the 2022-23 guideline amendment year, the Commission was considering whether to amend the Guidelines to allow a court to consider changes in law when deciding whether extraordinary and compelling reasons justify a sentence reduction under the compassionate release statute, 18 U.S.C. § 3582(c)(1)(A)(i), the positions at the Department — and on the Commission, too — were firm and uncompromising.
My then-colleagues in the Solicitor General’s Office, the Appellate Section of the Criminal Division, and the U.S. Attorney community had been arguing strenuously in courts across the country, since the enactment of the First Step Act in 2018, that compassionate release, as a matter of statutory law, could not be used to reduce a sentence on the basis of changes in law. The Act had given offenders for the first time the ability to move for compassionate release, and they were making this claim. The Department’s argument had been that there was nothing extraordinary about applying changes in law prospectively only. Rob Parker, the Chief of the Appellate Section, summarized the position this way in testimony before the Commission —
Applying a change in law prospectively is typical, not extraordinary, and although Courts of Appeals disagree on the meaning of extraordinary and compelling, they all agree that the expansion proposed here, which would make non-retroactive changes in law a stand-alone reason for compassionate release, is foreclosed by the Sentencing Reform Act.
Then-Commissioner John Gleeson, on the other hand — and on behalf of three other commissioners — was as resolved as Parker and the Department, but in the opposite direction. Gleeson had created, a few years earlier, the Holloway Project, a litigation initiative to reduce extraordinarily long sentences meted out under 18 U.S.C. § 924(c), the statute that provides mandatory minimum sentences for offenders who use or possess a firearm during a crime of violence or drug trafficking crime. The First Step Act, in addition to opening compassionate release motions to offenders themselves, reduced the 25-year mandatory minimum imprisonment term that had applied to second and subsequent violations of § 924(c) to five years, if the violations were part of a single criminal prosecution. But the Act didn’t apply the change retroactively. Hence Gleeson’s desire to find an alternative mechanism to provide relief to those already serving extraordinarily long § 924(c) sentences, which mostly ended up being compassionate release. Years before, as the presiding judge in United States v. Holloway, 68 F. Supp. 3d 310, 312 (EDNY 2014), Gleeson said that § 924(c) “produce[d] sentences that would be laughable if only there weren’t real people on the receiving end of them.”
Just as the Department and Gleeson were sharply at odds, so were the circuit courts of appeals, seemingly making both sides of the debate even more adamant in their positions. What was so particularly galling to Gleeson about the Department’s position at the Commission and later in the courts was that just a few years earlier, on several occasions, the Department successfully opposed Supreme Court review of the issue on the ground that the issue should be addressed first by the Commission. Gleeson repeatedly quoted back to me the Department’s own words from filings opposing certiorari petitions in the Supreme Court. “Nobody disputes . . . that the Commission has the power — indeed, the statutory duty — to promulgate a policy statement that applies to prisoner-filed motions, or that it could resolve this particular issue.” Yet now, the Department was arguing that the Commission lacked that very authority.
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It seemed almost a certainty that the changes in law provision would be approved by a divided Commission vote and that the Department would subsequently challenge the Commission’s authority to include changes in law in its definition of extraordinary and compelling. And it also seemed a near certainty that the issue would end up at the Supreme Court.
I thought the ultimate fight we were heading for was not in the best interest of the Department, the Commission, or justice. I thought a compromise might be forged between the factions that would be beneficial not only to avoid a confrontation about the Commission’s authority, but also to land on a better compassionate release policy. It struck me — especially from the testimony before the Commission — that compassionate release was really ultimately about whether the totality of circumstances in a particular case was extraordinary and compelling and warranted a sentence reduction, not just whether certain specific, narrow reasons spelled out in the Guidelines were met. Compassionate release should be, I thought, a genuine second look mechanism for offenders in extraordinary circumstances and not just a workaround for otherwise applicable criminal procedure barriers.
In testimony before the Commission on the published proposal, one witness said judges must look at “the entire constellation of circumstances, factually and legal” that might justify a reduction in sentence. Many witnesses testified about offenders who might have warranted a reduction and spoke mostly about how the offenders had made extraordinary progress toward changing their lives and were very different people than the ones who were originally sentenced. Yes, technical eligibility was a must, especially in light of the limitation, in 28 U.S.C. § 994(t), that “[r]ehabilitation of the defendant alone shall not be considered an extraordinary and compelling reason.” But the narrative was inevitably about reform and redemption.
I hoped it might be possible to find a way to capture the idea of the “constellation” of circumstances, in addition to the narrow medical and family circumstances justifying a sentence reduction, while simultaneously eliminating the use of compassionate release as a workaround to restrictions on retroactive application of changes in law or on collateral review of convictions and sentences. The way I defined my role as the Attorney General’s representative, it was my responsibility to try to forge that compromise.
With all that in mind, I drafted this modification to what the Commission was considering for its amendment to §1B1.13 —
(b) Change in Law or Challenge to the Validity of a Conviction or Sentence.—Modification of a sentence based on retroactive application of a change of law or a challenge to the validity of a conviction or sentence is not an appropriate use of 18 U.S.C. § 3582(c)(1)(A). However, if a defendant otherwise establishes that extraordinary and compelling reasons warrant a sentence reduction, such factors may be considered in determining whether and to what extent to reduce a term of imprisonment or to impose a term of probation or supervised release.
(c) Extraordinary and Compelling Reasons.—Extraordinary and compelling reasons exist under any of the following circumstances or a combination thereof . . .
(6) Totality of Circumstances.— Occasionally, the totality of circumstances surrounding a person serving an unusually long imprisonment sentence will have changed so substantially, including as a result of rehabilitation, a new family circumstance, legal developments, or a combination of these and other factors, to constitute extraordinary and compelling reasons. In determining whether and to what extent a sentence reduction is appropriate under this paragraph, the court may consider the person’s (A) in-prison program participation, (B) mental, physical and emotional conditions, (C) work record in custody, (D) record of good works, (E) assistance to others, and (F) efforts to mitigate the effects of the offense.
The proposal would authorize compassionate release in limited cases not constituting extraordinary medical or family circumstances but yet involving substantially changed individual circumstances. As a matter of law, this is, I believed, embodied in the words extraordinary and compelling and also in 18 U.S.C. § 3582(c)(1)(A)’s requirement to consider the purposes of sentencing and the other § 3553(a) factors. It would have been a step to creating a true second look provision for federal offenders sentenced to extraordinarily long imprisonment sentences. I thought it was a more just and better policy than either what my colleagues were pushing or what Judge Gleeson was pushing.
I met with the Deputy Attorney General’s Office to get it’s ok to propose the modification. They gave me the go-ahead. I then circulated it to the commissioners. It was rejected. There was no counter-suggestion, and there were no negotiations. The Commission later approved, on a vote of 4-3, what ultimately is now in §1B1.13, including that —
If a defendant received an unusually long sentence and has served at least 10 years of the term of imprisonment, a change in the law (other than an amendment to the Guidelines Manual that has not been made retroactive) may be considered in determining whether the defendant presents an extraordinary and compelling reason, but only where such change would produce a gross disparity between the sentence being served and the sentence likely to be imposed at the time the motion is filed, and after full consideration of the defendant’s individualized circumstances.
As expected, the Department challenged the Commission’s authority to promulgate the amendment. Over the next 18 months or so, the courts of appeals split on the issue, also as expected. And now three cases are set to be heard by the Supreme Court this coming term addressing the appropriate scope of compassionate release. I find it a shame that a better, more robust second look policy was not adopted and that the fight over changes in law — and how compassionate release intersects with § 2255 — has continued.
As we move closer to arguments now scheduled at the Court, I wonder if folks at the Commission are having any second thoughts about how they handled this in 2023? Are they considering — or might they consider — that with the circuits split over the Commission’s action and its authority to promulgate the changes in law provision, whether to reconsider the amendment to §1B1.13, even this very amendment cycle? If the Commission did take up the issue again, would it moot the pending Supreme Court cases? Is such action worth thinking about? And regardless, would the Commission consider a totality of circumstances guideline amendment after we get a ruling from the Supreme Court, either way?
The Supreme Court’s October 2025 term begins in about six weeks. As we move closer to it — and then as the term plays out over the following months — we’ll see what the Commission does and we’ll also see if justice ultimately prevails. And as we do, it’s worth contemplating both what compassionate release might have been and also what it might be in the future.
